TY - GEN A1 - Moerschbacher, Bruno A1 - Jaworska, Małgorzata A1 - Peter, Martin G. T1 - Obituary of George A.F. Roberts (1939-2018) T2 - Reactive & functional polymers Y1 - 2020 U6 - https://doi.org/10.1016/j.reactfunctpolym.2020.104711 SN - 1381-5148 SN - 1873-166X VL - 156 PB - Elsevier CY - Amsterdam [u.a.] ER - TY - JOUR A1 - Pereira, Fernanda S. A1 - Nascimento, Heliara D. L. A1 - Magalhaes, Alvicler A1 - Peter, Martin G. A1 - Bataglion, Giovana Anceski A1 - Eberlin, Marcos N. A1 - Gonzalez, Eduardo R. P. T1 - ESI(+)-MS and GC-MS study of the hydrolysis of N-azobenzyl derivatives of chitosan JF - Molecules N2 - New N-p-chloro-, N-p-bromo-, and N-p-nitrophenylazobenzylchitosan derivatives, as well as the corresponding azophenyl and azophenyl-p-sulfonic acids, were synthesized by coupling N-benzylvchitosan with aryl diazonium salts. The synthesized molecules were analyzed by UV-Vis, FT-IR, H-1-NMR and N-15-NMR spectroscopy. The capacity of copper chelation by these materials was studied by AAS. Chitosan and the derivatives were subjected to hydrolysis and the products were analyzed by ESI(+)-MS and GC-MS, confirming the formation of N-benzyl chitosan. Furthermore, the MS results indicate that a nucleophilic aromatic substitution (SnAr) reaction occurs under hydrolysis conditions, yielding chloroaniline from N-p-bromo-, and N-p-nitrophenylazo-benzylchitosan as well as bromoaniline from N-p-chloro-, and N-p-nitrophenylazobenzyl-chitosan. KW - chitosan KW - N-azobenzylchitosan KW - ESI-MS KW - GC-MS KW - SnAr reaction Y1 - 2014 U6 - https://doi.org/10.3390/molecules191117604 SN - 1420-3049 VL - 19 IS - 11 SP - 17604 EP - 17618 PB - MDPI CY - Basel ER - TY - JOUR A1 - Mengibar, M. A1 - Ganan, M. A1 - Miralles, B. A1 - Carrascosa, A. V. A1 - Martinez-Rodriguez, Adolfo J. A1 - Peter, Martin G. A1 - Heras, A. T1 - Antibacterial activity of products of depolymerization of chitosans with lysozyme and chitosanase against Campylobacter jejuni JF - Carbohydrate polymers : an international journal devoted to scientific and technological aspects of industrially important polysaccharides N2 - Chitosan has several biological properties useful for the food industry, but the most attractive is its potential use as a food preservative of natural origin due to its antimicrobial activity against a wide range of food-borne microorganisms. Among food-borne pathogens, Campylobacter jejuni and related species are recognised as the most common causes of bacterial food-borne diarrhoeal disease throughout the world. Recently, it has been demonstrated that campylobacters are highly sensitive to chitosan. Even though chitosan is known to have important functional activities, poor solubility makes them difficult to use in food and biomedical applications. Unlike chitosan, the low viscosity and good solubility of chitosan oligosaccharides (COS) make them especially attractive in an important number of useful applications. In the present work, the effect of different COS on C. jejuni was investigated. Variables such as the physicochemical characteristics of chitosan and the enzyme used in COS preparation were studied. The COS had been fractioned using ultrafiltration membranes and each fraction was characterized regarding its FA and molecular weight distribution. It has been demonstrated that the biological properties of COS on Campylobacter depend on the composition of the fraction analysed. COS prepared by enzymatic hydrolysis with chitosanase were more active against Campylobacter that lysozyme-derived COS, and this behaviour seems to be related with the acetylation of the chains. On the other hand. the 10-30 kDa fraction was the most active COS fraction, independently of the enzyme used for the hydrolysis. These results have shown that COS could be useful as antimicrobial in the control of C. jejuni. KW - Campylobacter jejuni KW - Chitooligosaccharides KW - Chitosanase KW - Lysozyme KW - Depolymerization Y1 - 2011 U6 - https://doi.org/10.1016/j.carbpol.2010.04.042 SN - 0144-8617 VL - 84 IS - 2 SP - 844 EP - 848 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Vijayakrishnan, Balakumar A1 - Issaree, Arisara A1 - Corilo, Yuri E. A1 - Ferreira, Christina Ramires A1 - Eberlin, Marcos N. A1 - Peter, Martin G. T1 - MSn of the six isomers of (GlcN)(2)(GlcNAc)(2) aminoglucan tetrasaccharides (diacetylchitotetraoses) rules of fragmentation for the sodiated molecules and application to sequence analysis of hetero-chitooligosaccharides JF - Carbohydrate polymers : an international journal devoted to scientific and technological aspects of industrially important polysaccharides N2 - The six possible isomers of di-N-acetylchitotetraoses [AADD, ADDA, ADAD, DADA, DAAD, and DDAA, where D stands for 2-amino-2-deoxy-3-D-glucose (GlcN) and A for 2-acetamido-2-deoxy-beta-D-glucose (GlcNAc)] were analyzed by ESI(+)-MSn. Collision induced dissociation via MSn experiments were performed for the sodiated molecules of m/z 769 [M+Na](+) for each isomer, and fragments were generated mainly by glycosidic bond and cross-ring cleavages. Rules of fragmentation were then established. A reducing end D residue yields the (O.2)A(4) cross-ring [M-59+Na](+) fragment of m/z 710 as the most abundant, whereas isomers containing a reducing end A prefer to lose water to form the [M-18+Na](+) ion of m/z 751, as well as abundant (O.2)A(4) cross-ring [M-101+Na](+) fragments of m/z 668 and B-3 [M-221+Na](+) ions of m/z 548. MS3 of C- and Y-type ions shows analogous fragmentation behaviour that allows identification of the reducing end next-neighbour residue. Due to gas-phase anchimeric assistance, B-type cleavage between the glycosidic oxygen and the anomeric carbon atom is favoured when the glycon is an A residue. Relative ion abundances are generally in the order B >> C > Y, but may vary depending on the next neighbour towards the non-reducing end. These fragmentation rules were used for partial sequence analysis of hetero-chitooligosaccharides of the composition D(2)A(3), D(3)A(3), D(2)A(4), D(4)A(3), and D(3)A(4). KW - Chitosan KW - Fragmentation KW - Oligosaccharides KW - Sequence analysis KW - Tandem mass spectrometry Y1 - 2011 U6 - https://doi.org/10.1016/j.carbpol.2010.04.041 SN - 0144-8617 VL - 84 IS - 2 SP - 713 EP - 726 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Juma, Wanyama P. A1 - Akala, Hoseah M. A1 - Eyase, Fredrick L. A1 - Muiva, Lois M. A1 - Heydenreich, Matthias A1 - Okalebo, Faith A. A1 - Gitu, Peter M. A1 - Peter, Martin G. A1 - Walsh, Douglas S. A1 - Imbuga, Mabel A1 - Yenesew, Abiy T1 - Terpurinflavone an antiplasmodial flavone from the stem of Tephrosia Purpurea JF - Phytochemistry letters N2 - The stem extract of Tephrosia purpurea showed antiplasmodial activity against the D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) strains of Plasmodium falciparum with IC(50) values of 10.47 +/- 2.22 mu g/ml and 12.06 +/- 2.54 mu g/ml, respectively. A new prenylated flavone, named terpurinflavone, along with the known compounds lanceolatin A, (-)-semiglabrin and lanceolatin B have been isolated from this extract. The new compound, terpurinflavone, showed the highest antiplasmodial activity with IC(50) values of 3.12 +/- 0.28 mu M (D6) and 6.26 +/- 2.66 mu M (W2). The structures were determined on the basis of spectroscopic evidence. KW - Tephrosia purpurea KW - Leguminosae KW - Stem KW - Flavone KW - Terpurinflavone KW - Antiplasmodial Y1 - 2011 U6 - https://doi.org/10.1016/j.phytol.2011.02.010 SN - 1874-3900 VL - 4 IS - 2 SP - 176 EP - 178 PB - Elsevier CY - Amsterdam ER - TY - JOUR A1 - Paz, Cristian A1 - Peter, Martin G. A1 - Schmidt, Bernd A1 - Becerra, Jose A1 - Gutierrez, Margarita A1 - Astudillo, Luis A1 - Silva, Mario T1 - Synthesis and AChE inhibiting activity of 2, 4 substituted 6-Phenyl Pyrimidines JF - Journal of the Chilean Chemical Society N2 - Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE. KW - Pyrimidines KW - inhibition AChE KW - mitsunobu KW - TBTU Y1 - 2012 SN - 0717-9324 VL - 57 IS - 3 SP - 1292 EP - 1294 PB - Sociedad Chilena De Quimica CY - Concepcion ER - TY - JOUR A1 - Fasciotti, Maira A1 - Sanvido, Gustavo B. A1 - Santos, Vanessa G. A1 - Lalli, Priscila M. A1 - McCullagh, Michael A1 - de Sa, Gilberto F. A1 - Daroda, Romeu J. A1 - Peter, Martin G. A1 - Eberlin, Marcos N. T1 - Separation of isomeric disaccharides by traveling wave ion mobility mass spectrometry using CO2 as drift gas JF - Journal of mass spectrometr N2 - The use of CO2 as a massive and polarizable drift gas is shown to greatly improve peak-to-peak resolution (Rp-p), as compared with N2, for the separation of disaccharides in a Synapt G2 traveling wave ion mobility cell. Near or baseline Rp-p was achieved for three pairs of sodiated molecules of disaccharide isomers, that is, cellobiose and sucrose (Rp-p?=?0.76), maltose and sucrose (Rp-p?=?1.04), and maltose and lactose (Rp-p?=?0.74). Ion mobility mass spectrometry using CO2 as the drift gas offers therefore an attractive alternative for fast and efficient separation of isomeric disaccharides. KW - isomer resolution KW - oligosaccharides KW - traveling wave ion mobility mass spectrometry KW - polarizable drift gases Y1 - 2012 U6 - https://doi.org/10.1002/jms.3089 SN - 1076-5174 VL - 47 IS - 12 SP - 1643 EP - 1647 PB - Wiley-Blackwell CY - Hoboken ER - TY - JOUR A1 - Andayi, Andrew W. A1 - Yenesew, Abiy A1 - Derese, Solomon A1 - Midiwo, Jacob O. A1 - Gitu, Peter M. A1 - Jondiko, Ogoche J. I. A1 - Akala, Hoseah M. A1 - Liyala, Pamela A1 - Wangui, Julia A1 - Waters, Norman C. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Antiplasmodial flavonoids from Erythrina sacleuxii N2 - The acetone extracts of the root bark and stem bark of Erythrina sacleuxii showed antiplasmodial activities against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Chromatographic separation of the acetone extract of the root bark afforded a new isoflavone, 7-hydroxy-4 -methoxy-3'- prenylisoflavone (trivial name 5-deoxy-3' - prenylbiochanin A) along with known isoflavonoids as the antiplasmodial principles. Flavonoids and isoflavonoids isolated from the stem bark of E. sucleuxii were also tested and showed antiplasmodial activities. The structures were determined on the basis of spectroscopic evidence Y1 - 2006 UR - http://www.thieme-connect.com/ejournals/toc/plantamedica U6 - https://doi.org/10.1055/s-2005-873200 SN - 0032-0943 ER - TY - JOUR A1 - Haebel, Sophie A1 - Bahrke, Sven A1 - Peter, Martin G. T1 - Quantitative sequencing of complex mixtures of heterochitooligosaccharides by vMALDI-linear ion trap mass spectrometry N2 - Heterochitooligosaccharides possess interesting biol. properties. Isobaric mixts. of such linear heterochitooligosaccharides can be obtained by chem. or enzymic degrdn. of chitosan. However, the sepn. of such mixts. is a challenging anal. problem which is so far unresolved. It is shown that these isobaric mixts. can be sequenced and quantified simultaneously using std. derivatization and multistage tandem mass spectrometric techniques. A linear ion trap mass spectrometer equipped with a vacuum matrix-assisted laser desorption ionization (vMALDI) source is used to perform MS2 as well as MS3 expts. [on SciFinder (R)]. Y1 - 2007 UR - http://pubs.acs.org/loi/ancham U6 - https://doi.org/10.1021/Ac062254u SN - 0003-2700 ER - TY - JOUR A1 - Norledge, Brian V. A1 - Lambeir, Anne M. A1 - Abagyan, Ruben A1 - Rottmann, Antje A1 - Fernendez, Anna M. A1 - Filimonov, Vladimir V. A1 - Peter, Martin G. A1 - Wierenga, Rik K. T1 - Modeling, mutagenesis, and structural studies on the fully conserved phoshate-binding loop (Loop 8) of triosephosphate isomerase : toward a new substrate specificity Y1 - 2001 UR - http://www3.interscience.wiley.com/journal/36176/toc SN - 0887-2585 ER - TY - JOUR A1 - Tsukamoto, Junko A1 - Haebel, Sophie A1 - Valenca, Gustavo P. A1 - Peter, Martin G. A1 - FRanco, Telma T. T1 - Enzymatic direct synthesis of acrylic acid esters of mono- and disaccharides N2 - Background: There is an increased need to replace materials derived from fossil sources by renewables. Sugar- cane derived carbohydrates are very abundant in Brazil and are the cheapest sugars available in the market, with more than 400 million tons of sugarcane processed in the year 2007. The objective of this work was to study the prepn. of sugar acrylates from free sugars and free acrylic acid, thus avoiding the previous prepn. of protected sugar derivs., such as glycosides, or activated acrylates, such as vinyl acrylate. Results: Lipase catalyzed esterification of three mono- and two disaccharides with acrylic acid, in the presence or absence of mol. sieves was investigated. The reactions were monitored by high-performance liq. chromatog. (HPLC) and the products were analyzed by matrix-assisted laser desorption ionization-time of flight (MALDI-TOF) mass spectrometry. The main products are mono- and diacrylates, while higher esters are formed as minor products. The highest conversion to sugar acrylates was obsd. for the D-glucose and D- fructose, followed by D-xylose and D-maltose. Mol. sieves had no pronounced effect on the conversion. Conclusions: A feasible method is described to produce and to characterize sugar acrylates, including those contg. more than two acrylate groups. The process for prodn. of these higher esters could potentially be optimized further to produce mols. for crosslinking in acrylate polymn. and other applications. The direct enzymic esterification of free carbohydrates with acrylic acid is unprecedented. [on SciFinder (R)]. Y1 - 2008 UR - http://www3.interscience.wiley.com/journal/117946200/grouphome/home.html SN - 0268-2575 ER - TY - JOUR A1 - López-Franco, Yolanda L. A1 - Calderón de la Barca, Ana M. A1 - Valdez, Miguel A. A1 - Peter, Martin G. A1 - Rinaudo, Marguerite A1 - Chambat, Gérard A1 - Goycoolea, Francisco M. T1 - Structural characterization of mesquite (Prosopis velutina) gum and its fractions N2 - Structural and physicochem. characteristics of mesquite gum (from Prosopis velutina) were investigated using FT- IR spectroscopic, mass spectrometric and chromatog. methods. Four fractions (F-I, F-IIa, F-IIb and F-III) were isolated by hydrophobic interaction chromatog. The samples were characterized and analyzed for their monosaccharide and oligomers compn. by high performance anion-exchange chromatog. with pulsed amperometric detection (HPAEC-PAD). L-Arabinose (L-Ara) and D-galactose (D-Gal) were found as the main carbohydrate constituent residues in the polysaccharides from mesquite gum and their ratio (L-Ara/D-Gal) varied within the range 2.54 to 3.06 among the various fractions. Small amts. of D- glucose (D-Glc), D-mannose (D-Man) and D-xylose (D-Xyl) were also detected, particularly in Fractions IIa, IIb and III. IR spectroscopy identified polysaccharides and protein in all the samples. Data from mass spectrometry (MALDI-TOF MS) was consistent with the idea that the structure corresponding to the periphereal chains of Fraction I is predominantly a chain of pentoses attached to uronic acid. [on SciFinder (R)]. Y1 - 2008 UR - http://www3.interscience.wiley.com/journal/77002860/home?CRETRY=1&SRETRY=0 U6 - https://doi.org/10.1002/mabi.200700285 SN - 1616-5187 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Twinomuhwezi, Hannington A1 - Kiremire, Bernard T. A1 - Mbugua, Martin N. A1 - Gitu, Peter M. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - 8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica N2 - A new pterocarpan (named 8-methoxyneorautenol) was isolated from the acetone ext. of the root bark of Erythrina abyssinica. In addn., the known isoflavonoid derivs. eryvarin L, erycristagallin and shinpterocarpin were identified for the first time from the roots of this plant. The structures were detd. on the basis of spectroscopic evidence. The new compd. showed selective antimicrobial activity against Trichophyton mentagrophytes. The acetone ext. of the root bark of E. abyssinica showed radical scavenging activity towards 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The pterocarpenes, 3-hydroxy-9-methoxy-10-(3,3-dimethylallyl)pterocarpene and erycristagallin, were the most active constituents of the roots of this plant and showing dose-dependent activities similar to that of the std. quercetin. [on SciFinder (R)] Y1 - 2009 UR - http://www.ajol.info/journal_index.php?jid=120&ab=bcse SN - 1011-3924 ER - TY - JOUR A1 - Fettke, Anja A1 - Peikow, Dirk A1 - Peter, Martin G. A1 - Kleinpeter, Erich T1 - Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose N2 - The synthesis of six analogs of N,N;-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, ;; and ;; and of the S-arylglycoside bonds, ; and ;, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies. Y1 - 2009 UR - http://www.sciencedirect.com/science/journal/00404020 U6 - https://doi.org/10.1016/j.tet.2009.03.067 SN - 0040-4020 ER - TY - JOUR A1 - Menezes, Bruno M. A1 - Grigolon, Lisanne A1 - Todorovic, Zoran A1 - Peter, Martin G. A1 - Franco, Telma T. T1 - On the depolymerization of chitosan by papain : a re-assessment Y1 - 2009 ER - TY - JOUR A1 - Oliveira, Enio N. A1 - el Gueddari, Nour E. A1 - Moerschbacher, Bruno M. A1 - Peter, Martin G. A1 - Franco, Telma T. T1 - Growth of phytopathogenic fungi in the presence of partially acetylated chitooligosaccharides N2 - Four phytopathogenic fungi were cultivated up to six days in media contg. chitooligosaccharide mixts. differing in av. DP and F A. The three different mixts. were named Q3 (which contained oligosaccharides of DP2-DP10, with DP2-DP7 as main components), Q2 (which contained oligosaccharides of DP2-DP12, with DP2-DP10 as main components) and Q1 (which derived from Q2 and contained oligomers of DP5-DP8 with hexamer and a heptamer as the main components). The novel aspect of this work is the description of the effect of mixts. of oligosaccharides with different and known compn. on fungal growth rates. The growth rate of Alternaria alternata and Rhizopus stolonifer was initially inhibited by Q3 and Q2 at higher concns. Q1 had a growth stimulating effect on these two fungi. Growth of Botrytis cinerea was inhibited by Q3 and Q2, while Q1 had no effect on the growth of this fungus. Growth of Penicillium expansum was only slightly inhibited by higher concns. of sample Q3, while Q2 and Q1 had no effect. The inhibition of growth rates or their resistance toward chitooligosaccharides correlated with the absence or presence of chitinolytic enzymes in the culture media, resp. [on SciFinder (R)] Y1 - 2008 UR - http://www.springerlink.com/content/102966 SN - 0301-486X ER - TY - JOUR A1 - Bringmann, Gerhard A1 - Mutanyatta-Comar, Joan A1 - Maksimenka, Katja A1 - Wanjohi, John M. A1 - Heydenreich, Matthias A1 - Brun, Reto A1 - Müller, Werner E. G. A1 - Peter, Martin G. A1 - Midiwo, Jacob O. A1 - Yenesew, Abiy T1 - Joziknipholones A and B : the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens N2 - From the roots of the African plant Bulbine frutescens (Asphodelaceae), two unprecedented novel dimeric phenylanthraquinones, named joziknipholones A and B, possessing axial and centrochirality, were isolated, together with six known compounds. Structural elucidation of the new metabolites was achieved by spectroscopic and chiroptical methods, by reductive cleavage of the central bond between the monomeric phenylanthraquinone and -anthrone portions with sodium dithionite, and by quantum chemical CD calculations. Based on the recently revised absolute axial configuration of the parent phenylanthraquinones, knipholone and knipholone anthrone, the new dimers were attributed to possess the P- configuration (i.e., with the acetyl portions below the anthraquinone plane) at both axes in the case of joziknipholone A, whereas in joziknipholone B, the knipholone part was found to be M-configured. Joziknipholones A and B are active against the chloroquine resistant strain K1 of the malaria pathogen, Plasmodium falciparum, and show moderate activity against murine leukemic lymphoma L5178y cells. Y1 - 2008 UR - http://www3.interscience.wiley.com/journal/26293/home?CRETRY=1&SRETRY=0 SN - 0947-6539 ER - TY - JOUR A1 - Rukunga, G. M. A1 - Muregi, F. W. A1 - Omar, S. A. A1 - Gathirwa, J. W. A1 - Muthaura, C. N. A1 - Peter, Martin G. T1 - Anti-plasmodial activity of the extracts and two sesquiterpenes from Cyperus articulatus N2 - Two sesquiterpenes, corymbolone and mustakone, isolated from the chloroform extract of the rhizomes of Cyperus articulatus, exhibited significant anti-plasmodial properties. Mustakone was approximately ten times more active than corymbolone against the sensitive strains of the Plasmodium falciparum. Y1 - 2008 SN - 0367-326X ER - TY - JOUR A1 - Issaree, Arisara A1 - Vijayakrishnan, Balakumar A1 - Abdelnur, Patricia V. A1 - Corilo, Yuri E. A1 - Riccio, Maria F. A1 - Sanvido, Gustavo B. A1 - Eberlin, Marcos N. A1 - Peter, Martin G. T1 - Mass spectrometry of aminoglucan oligosaccharides using electrospray ionization MS/MS and MS/MS/MS Y1 - 2009 ER - TY - JOUR A1 - Peter, Martin G. A1 - Ley, J. P. A1 - Petersen, Stefan A1 - Londershausen, M. A1 - Schumacher-Wandersleb, Michael H. M. G. A1 - Spindler, Klaus-Dieter A1 - Spindler-Barth, Margarethe A1 - Turberg, Andreas T1 - Synthesis of chitinase inhibitors Y1 - 1994 ER - TY - JOUR A1 - Krösche, Christian A1 - Crescenzi, Orlando A1 - Hoffbauer, Wilfried A1 - Jansen, Martin A1 - Napolitano, Alessandra A1 - Prota, Guiseppe A1 - Peter, Martin G. T1 - Synthesis of dopamines labelled with 13C in the alpha- or beta-side chain positions, and their application for structure studies on melanins by solid state NMR spectroscopy Y1 - 1994 ER - TY - JOUR A1 - Schumacher-Wandersleb, Michael H. M. G. A1 - Petersen, Stefan A1 - Peter, Martin G. T1 - Preparation of the N-Acetylglucosaminidase inhibitor 1-Acetamido-1,2,5-tride oxy-2,5-imino-D-glucitol from methyl a-D-Mannopyranoside Y1 - 1994 ER - TY - JOUR A1 - Peter, Martin G. A1 - Andersen, S. O. T1 - The molecular architecture of the insect exoskeleton Y1 - 1994 ER - TY - JOUR A1 - Ley, J. P. A1 - Peter, Martin G. T1 - Synthesis of N-(2-Acetamido-2-deoxy-ß-D-glucopyranosyl)- and of N-(N,N-Diacetylchitobiosyl)-amide of lhistidine Y1 - 1994 SN - 0039-7881 ER - TY - JOUR A1 - Schumacher-Wandersleb, Michael H. M. G. A1 - Peter, Martin G. T1 - Synthesis of chitobiosyl pyrrolidines Y1 - 1995 ER - TY - JOUR A1 - Peter, Martin G. A1 - Merz, A. T1 - Stereoselective benzylic deprotonation in the enzymatic rearrangement of N-acetyldopamine derived o-Quinone to the p-Quinone methide Y1 - 1995 SN - 0957-4166 ER - TY - JOUR A1 - Peter, Martin G. T1 - Chitin in den Startlöchern Y1 - 1995 SN - 0009-2959 ER - TY - JOUR A1 - Peter, Martin G. T1 - Chemistry and biochemistry of the insect exoskeleton Y1 - 1995 ER - TY - JOUR A1 - Peter, Martin G. T1 - Chemie i Biochemia Zewnetrznego Szkieletu Owadow : (Chemistry and biochemistry of the insect exoskeleton) Y1 - 1995 ER - TY - JOUR A1 - Peter, Martin G. T1 - The Bio-organic chemistry of melanogenesis Y1 - 1995 ER - TY - JOUR A1 - Abegaz, Berhanu M. A1 - Peter, Martin G. T1 - Emodine and emodinanthrone rhamnoside acetates from fruits of rhamnus prinoides Y1 - 1995 SN - 0031-9422 ER - TY - JOUR A1 - Peter, Martin G. T1 - Applications and environmental aspects of chitin and chitosan Y1 - 1995 SN - 0022-233X ER - TY - JOUR A1 - Buss, U. A1 - Varum, K. M. A1 - Peter, Martin G. A1 - Spindler-Barth, Margarethe T1 - ELISA for quantitation of chitin, chitosan and related compounds Y1 - 1996 ER - TY - JOUR A1 - Ley, J. P. A1 - Peter, Martin G. T1 - Synthesis of L-histidine and (-)-spinacine chitooligosyl amides Y1 - 1996 ER - TY - JOUR A1 - Krösche, Ch. A1 - Peter, Martin G. T1 - Detection of melanochromes by MALDI-TOF mass spectrometry Y1 - 1996 ER - TY - JOUR A1 - Andersen, S. O. A1 - Peter, Martin G. A1 - Roepstorff, Peter T1 - Cuticular sclerotization in insects Y1 - 1996 ER - TY - JOUR A1 - Londershausen, M. A1 - Turberg, Andreas A1 - Spindler-Barth, Margarethe A1 - Peter, Martin G. T1 - Screening Test for Insecticides Interfering with Cuticular Sclerotization Y1 - 1996 ER - TY - JOUR A1 - Londershausen, M. A1 - Turberg, Andreas A1 - Bieseler, Barbara A1 - Lennarz, M. A1 - Peter, Martin G. T1 - Characterization and Inhibitor Studies of Chitinases from Parasitic Blowfly (Lucilia cuprina), Tick (Boophilus micoplus), Intestinale Nematode (Haemonchus contortus), and a Bean (Phaseolus vulgaris) Y1 - 1996 ER - TY - JOUR A1 - Peter, Martin G. A1 - Miessner, Merle T1 - Primärstoffwechsel, Shikimat- und Phenylpropan-Gruppe, Vitamine, Coenzyme, Pflanzeninhaltsstoffe Y1 - 1997 ER - TY - JOUR A1 - Schanzenbach, Dirk A1 - Peter, Martin G. T1 - Chromatography of chito-oligosaccarides Y1 - 1997 ER - TY - JOUR A1 - Ley, J. P. A1 - Schweikart, F. A1 - Peter, Martin G. T1 - Chitinase inhibitors Y1 - 1997 ER - TY - JOUR A1 - Schanzenbach, Dirk A1 - Matern, Christa-Maria A1 - Peter, Martin G. T1 - Synthesis of glycosylamines and glycopeptides Y1 - 1997 ER - TY - JOUR A1 - Schanzenbach, Dirk A1 - Peter, Martin G. T1 - NMR spectroscopy of chito-oligosaccharides Y1 - 1997 ER - TY - JOUR A1 - Schanzenbach, Dirk A1 - Matern, Christa-Maria A1 - Peter, Martin G. T1 - Cleavage of chitin by means of sulfurice acid/acetc anhydride and isolation of peracetylated chito- oligosaccharides Y1 - 1997 ER - TY - JOUR A1 - Ratajska, M. A1 - Struszczyk, Marcin Henryk A1 - Boryniec, Stefan A1 - Peter, Martin G. A1 - Loth, Fritz T1 - The degree of acetylation of chitosan : optimization of the IR Method Y1 - 1997 ER - TY - JOUR A1 - Peter, Martin G. A1 - Wollenberger, Ursula T1 - Phenol-oxidizing enzymes : mechanisms and applications Y1 - 1997 ER - TY - JOUR A1 - Haebel, Sophie A1 - Peter-Katalinic, Jasna A1 - Peter, Martin G. T1 - Mass spectrometry of chitooligosaccharides Y1 - 1997 SN - 88-86889- 01-1 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Ratajska, M. A1 - Boryniec, Stefan A1 - Peter, Martin G. A1 - Loth, Fritz T1 - The determination of the degree of N-acetylation of chitosan Y1 - 1997 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Peter, Martin G. T1 - Analysis of deacetylation deree in chitosans from various sources Y1 - 1998 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Köhler, L. A. A1 - Peter, Martin G. T1 - Characterization of chitosan Y1 - 1998 ER - TY - JOUR A1 - Berth, Gisela A1 - Dautzenberg, Herbert A1 - Peter, Martin G. T1 - Physico-chemical characterization of chitosans varying in degree of acetylation Y1 - 1998 SN - 0144-8617 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Four isoflavanones from stem bark of erythrina sacleuxii Y1 - 1998 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Meisner, M. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Two prenylated flavanones from stem bark of erythrina burttii Y1 - 1998 ER - TY - JOUR A1 - Streffer, Katrin A1 - Kaatz, Helvi A1 - Bauer, Christian G. A1 - Makower, Alexander A1 - Schulmeister, Thomas A1 - Scheller, Frieder W. A1 - Peter, Martin G. A1 - Wollenberger, Ursula T1 - Application of a sensitive catechol detector for determination of tyrosinase inhibitors Y1 - 1998 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Peter, Martin G. T1 - Calibration of methods for the determination of the degree of decatetylation of chitosan Y1 - 1998 ER - TY - JOUR A1 - Alarcon, Julio A1 - Alderete, Joel B. A1 - Peter, Martin G. A1 - Becerra, Juan J. A1 - Silva, M. T1 - Study on synthesis of 3 alpha,4 alpha-dihydroxy-dihydro-beta-agarofuran Y1 - 1998 ER - TY - JOUR A1 - Kamlage, Stefan A1 - Sefkow, Michael A1 - Peter, Martin G. T1 - Cross coupling of benzylic bromides and vinyl stannanes Y1 - 1999 ER - TY - JOUR A1 - Kaatz, Helvi A1 - Streffer, Katrin A1 - Wollenberger, Ursula A1 - Peter, Martin G. T1 - Inhibition of mushroom tyrosinase by kojic acid octanoates Y1 - 1999 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Peter, Martin G. T1 - Method of microcrystalline chitosan-protein films preparation Y1 - 1999 ER - TY - JOUR A1 - Rottmann, Antje A1 - Synstad, Bjoenar A1 - Thiele, G. A1 - Schanzenbach, Dirk A1 - Eijsink, Vincent G. H. A1 - Peter, Martin G. T1 - Approaches towards the design of new chitinase inhibitors Y1 - 1999 SN - 3-9806494-5-8 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Peter, Martin G. T1 - Preparation of paper sheets containing microcrystalline chitosan Y1 - 1999 SN - 3-9806494-5-8 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Halweg, R. A1 - Peter, Martin G. T1 - Comparative analysis of chitosans from insects and crustacea Y1 - 1999 SN - 3-9806494-5-8 ER - TY - JOUR A1 - Letzel, Matthias C. A1 - Synstad, Bjoenar A1 - Eijsink, Vincent G. H. A1 - Peter-Katalinic, Jasna A1 - Peter, Martin G. T1 - Libraries of chito-oligosaccharides of mixed acetylation patterns and their interactions with chitinases Y1 - 1999 SN - 3-9806494-5-8 ER - TY - JOUR A1 - Rottmann, Antje A1 - Synstad, Bjoenar A1 - Eijsink, Vincent G. H. A1 - Peter, Martin G. T1 - Synthesis of N-acetylglucosaminyl and diacetylchitobiosyl amides of heterocyclic carboxylic acids as potential chitinase inhibitors Y1 - 1999 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Peter, Martin G. T1 - Properties of microcrystalline chitosan gel-like dispersion and formed films Y1 - 2000 ER - TY - JOUR A1 - Becker, Thomas W. A1 - Peter, Martin G. A1 - Pool-Zobel, Beatrice L. T1 - Cellular effects of lignans : modulation of growth, oxidative DNA damage and cell metabolism in human colon cancer cells Y1 - 2000 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Schanzenbach, Dirk A1 - Peter, Martin G. T1 - Two Isoflavanones from the Stem Bark of Erythrina sacleuxii N2 - From the stem bark of Erythrina sacleuxii two new isoflavanones, (R)-5,7-dihydroxy-2',4',5'- trimethoxyisoflavanone (trivial name, (R)-2,3-dihydro-7-demethylrobustigenin) and (R)-5-hydroxy- 2',4',5'-trimethoxy-2'',2''- dimethylpyrano[5'',6'':6,7]isoflavanone (trivial name, (R)-saclenone) were isolated. In addition the known compounds shinpterocarpin, 2,3-dehydrokievitone, abyssinone V, abyssinone V-4'-methyl ether, erythrinasinate and 4'-O-methylsigmoidin B were isolated. The structures were determined on the basis of spectroscopic evidence. Y1 - 2000 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Pospieszny, Henryk A1 - Schanzenbach, Dirk A1 - Peter, Martin G. T1 - Biodegradation of various chitosans using Aspergillus fumigatus Y1 - 2001 ER - TY - JOUR A1 - Zala, Eva A1 - Struszczyk, Marcin Henryk A1 - Peter, Martin G. T1 - Effects of preparation methods for chitosan films on their properties Y1 - 2001 ER - TY - JOUR A1 - Struszczyk, Marcin Henryk A1 - Loth, Fritz A1 - Pospieszny, Henryk A1 - Peter, Martin G. T1 - Biodegradation of films and paper sheets containing chitosan Y1 - 2001 ER - TY - JOUR A1 - Letzel, Matthias C. A1 - Peter-Katalinic, Jasna A1 - Peter, Martin G. T1 - Mass spectrometry of chitin and chitosan oligosaccharides Y1 - 2001 ER - TY - JOUR A1 - Peter, Martin G. T1 - Structures of Chitinases and the Design of Inhibitors Y1 - 2001 ER - TY - JOUR A1 - Kamlage, Stefan A1 - Sefkow, Michael A1 - Peter, Martin G. T1 - A short synthesis of biologically active lignan analogues N2 - beta-Benzyl-gamma-butyrolactones were synthesized in four transition metal catalysed reactions from butynediol, and alkylated to afford new, biologically active lignan analogues. Y1 - 2001 ER - TY - JOUR A1 - Peter, Martin G. T1 - Natürliche Klebstoffe : von Muscheln, Seepocken, Spinnen und anderem Klebe-Getier Y1 - 2001 SN - 3-519-16195-8 ER - TY - JOUR A1 - Miessner, Merle A1 - Peter, Martin G. A1 - Vincent, Julian F. V. T1 - Preparation of Insect-Cuticle-Like Biomimetic Materials N2 - A model system of tanning of a protein matrix within a fibrous structure, such as most commonly found in insect cuticle, was developed, using the cellulose of paper in place of chitin. The paper was impregnated with a tripeptide, DOPA-Gly-Gly, or a protein (BSA) plus catechol and treated with tyrosinase to oxidize the catechol. The resulting material was waterproof and had very high wet strength. If the material was wetted and dried repeatedly its water retention decreased by a factor of at least two. Y1 - 2001 ER - TY - JOUR A1 - van Aalten, Daan M. F. A1 - Komander, David A1 - Synstad, Bjoenar A1 - Gaseidnes, Sigrid A1 - Peter, Martin G. A1 - Eijsink, Vincent G. H. T1 - Structural Insights into the catalytic mechanism of a family 18 exochitinase N2 - Chitinase B (ChiB) from Serratia marcescens is a family 18 exochitinase whose catalytic domain has a TIM-barrel fold with a tunnel-shaped active site. We have solved structures of three ChiB complexes that reveal details of substrate binding, substrateassisted catalysis, and product displacement. The structure of an inactive ChiB mutant (E144Q) complexed with a pentameric substrate (binding in subsites 22 to 13) shows closure of the ''roof'' of the active site tunnel. It also shows that the sugar in the 21 position is distorted to a boat conformation, thus providing structural evidence in support of a previously proposed catalytic mechanism. The structures of the active enzyme complexed to Allosamidin (an analogue of a proposed reaction intermediate) and of the active enzyme soaked with pentameric substrate show events after cleavage of the glycosidic bond. The latter structure shows reopening of the roof of the active site tunnel and enzyme-assisted product displacement in the 11 and 12 sites, allowing a water molecule to approach the reaction center. Catalysis is accompanied by correlated structural changes in the core of the TIM barrel that involve conserved polar residues whose functions were hitherto unknown. These changes simultaneously contribute to stabilization of the reaction intermediate and alternation of the pKa of the catalytic acid during the catalytic cycle. Y1 - 2002 ER - TY - JOUR A1 - Houston, Douglas R. A1 - Shiomi, Kazuro A1 - Arai, Noriko A1 - Omura, Satoshi A1 - Peter, Martin G. A1 - Turberg, Andreas A1 - Synstad, Bjoenar A1 - Eijsink, Vincent G. H. A1 - Van Aalten, Daan M. F. T1 - High-resolution structures of a chitinase complexed with natural product cyclopentapeptide inhibitors : mimicry of carbohydrate substrate N2 - Over the past years, family 18 chitinases have been validated as potential targets for the design of drugs against human pathogens that contain or interact with chitin during their normal life cycles. Thus far, only one potent chitinase inhibitor has been described in detail, the pseudotrisaccharide allosamidin. Recently, however, two potent natural-product cyclopentapeptide chitinase inhibitors, argifin and argadin, were reported. Here, we describe high- resoln. crystal structures that reveal the details of the interactions of these cyclopeptides with a family 18 chitinase. The structures are examples of complexes of a carbohydrate-processing enzyme with high-affinity peptide-based inhibitors and show in detail how the peptide backbone and side chains mimic the interactions of the enzyme with chitooligosaccharides. Together with enzymol. characterization, the structures explain why argadin shows an order of magnitude stronger inhibition than allosamidin, whereas argifin shows weaker inhibition. The peptides bind to the chitinase in remarkably different ways, which may explain the differences in inhibition consts. The two complexes provide a basis for structure-based design of potent chitinase inhibitors, accessible by std. peptide chem. Y1 - 2002 ER - TY - JOUR A1 - Germer, Antje A1 - Klod, Sabrina A1 - Peter, Martin G. A1 - Kleinpeter, Erich T1 - NMR spectroscopic and theoretical study of the complexation of the inhibitor allosamidin in the binding pocket of the plant chitinase hevamine N2 - Based on NMR spectroscopic information about the allosamidin-hevamine complex, ab initio MO calcns. of the ring current effect of the arom. moieties of Trp255, Tyr183 and Tyr6 of hevamine were carried out to investigate the role of these amino acid residues in binding interactions with allosamidin in soln. In addn., the intermol. steric compression effect on the 13C chem. shifts of the allosamizoline carbon atoms and the hydrogen bonding to Glu127 was identified. It can be inferred that the binding forces are strongest in the allosamizoline moiety of allosamidin. Y1 - 2002 ER - TY - JOUR A1 - Thiele, Gabriela A1 - Rottmann, Antje A1 - Germer, Antje A1 - Kleinpeter, Erich A1 - Spindler, Klaus-Dieter A1 - Synstad, Bjoenar A1 - Eijsink, Vincent G. H. A1 - Peter, Martin G. T1 - Synthesis and conformational analysis of pseudosugar analogues of chitotriose N2 - In this article, the synthesis of analogs of N,N',N''-triacetylchitotriose in which the central sugar residue was replaced by a succinic acid is presented. Mol. modeling calcns. revealed that the pseudotrisaccharides exist in low energy extended conformations which show similar space filling as N,N',N''-triacetylchitotriose. Of the N,N',N''-triacetylchitotriose pseudosugar analogs tested as chitinase inhibitors, none showed any appreciable competition (numerical data not presented). The conformational anal. along with further synthetic efforts will hopefully lead to more efficient pseudosaccharides as chitinase inhibitors. Y1 - 2002 ER - TY - JOUR A1 - Bahrke, Sven A1 - Einarsson, Jon M. A1 - Gislason, Johannes A1 - Haebel, Sophie A1 - Letzel, Matthias C. A1 - Peter-Katalinic, Jasna A1 - Peter, Martin G. T1 - Sequence analysis of chitooligosaccharides by matrix-assisted laser desorption ionization postsource decay mass spectrometry N2 - Oligosaccharides composed of 2-acetamido-2-deoxy-D-glucopyranose (GlcNAc) and/or 2-amino-2-deoxy-D- glucopyranose (GlcN) were prepd. by chem. degrdn. of chitin or chitosan and sepd. by gel permeation chromatog. Oligosaccharides obtained after enzymic hydrolysis of chitosan [FA 0.19] with a fungal chitinase were derivatized by reductive amination with 2-aminoacridone and sequenced by matrix-assisted laser desorption ionization time-of-flight postsource decay (PSD) mass spectrometry (MS). The sequence of a trimer, D1A2, was established as D-A-A. The compn. of a hexamer D3A3 was .apprx.65% D-A-D-D-A-A and 35% D-D-A-D-A-A. The PSD MS of a nonamer D5A4-amac revealed four isobaric species D-X-Y-D-X-Y-D-A-A, where A is GlcNAc, D is GlcN, and X and Y (X ¹ Y) are mutually either D or A. This structure motif was also obsd. in a dodecamer D7A5 which was composed of eight isobaric sequences of the general formula (D-X-Y)3- D-A-A. Y1 - 2002 ER - TY - JOUR A1 - Germer, Antje A1 - Peter, Martin G. A1 - Kleinpeter, Erich T1 - Solution-state conformational study of the hevamine inhibitor allosamidin and six potential inhibitor analogues by NMR spectroscopy and molecular modeling N2 - The soln.-state conformations of the hevamine inhibitor allosamidin and six potential inhibitor analogs were studied by various NMR spectroscopic techniques and mol. modeling using force field calcns. Detn. solely of the global energy min. conformation was found to be insufficient for consensus with the NMR results, and agreement between the NMR exptl. data and the theor. calcns. was only reached by assessing the structures as population-weighted av. conformers on the basis of Boltzmann distributions derived from the calcd. relative energies. The conformations of the glycosidic linkages in the compds. were found to be similar when the sugar residues were the same, but differences were markedly evident otherwise and also for the various heterocyclic group linkages. The binding of the compds. to hevamine, which may also complex to chitinases in general, was assessed using HMQC, transfer-NOESY, and both 1-D and 2-D satn. transfer difference NMR expts. Under the conditions employed, only allosamidin was implicated to be bound to hevamine, and then only by HMQC with the dipolar coupling-based expts. failing to substantiate the formation of the complex. However, the results are consistent with the biochem. activities of the compds. whereby only allosamidin has been shown to act as a competitive inhibitor. Y1 - 2002 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Guchu, S. M. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Three iosoflav-3-enes and a 2-arylbenzofuran from the root bark of Erythrina burttii N2 - From the root bark of Erythrina burttii three new isoflav-3-enes, 7,4'-dihydroxy-2'-methoxy-6- (1'',1''-dimethylallyl)isoflav-3-ene (trivial name, burttinol-A), 4'-hydroxy-2'- methoxy-(2'',2''-dimethylpyrano[5'',6'':8,7]isoflav-3-ene (trivial name, burttinol-B), 7,4'-dihydroxy-2'-methoxy-8-(3'',3''-dimethylallyl)isoflav-3-ene (trivial name, burttinol-C), and a new 2-arylbenzofuran, 6,4'-dihydroxy-2'-methoxy-5- (1'',1''-dimethylallyl)-2-arylbenzofuran (trivial name, burttinol-D) were isolated. In addition, the known compounds, abyssinone V-4'-methyl ether, bidwillol A, calopocarpin, erybraedin A, erythrabyssin II, isobavachalcone, phaseollidin and phaseollin were identified. The structures were determined on the basis of spectroscopic evidence. Y1 - 2002 ER - TY - JOUR A1 - Peter, Martin G. T1 - Chitin and Chitosan from Animal Sources N2 - A review on the chem. and biochem. of chitin and the chem. and application of chitosan. The following topics were discussed: structure of chitin and chitosan; occurrence and physiol. functions of chitin; detection of chitin in animals and anal. of chitin and chitosan; biosynthesis and biodegrdn. of chitin in animals; prodn. of chitin and chitosan; properties of chitin and chitosan; and applications of chitin and chitosan. Y1 - 2002 SN - 3-527-30227-1 ER - TY - JOUR A1 - Peter, Martin G. T1 - Chitin and Chitosan from Fungi Y1 - 2002 SN - 3-527-30227-1 ER - TY - JOUR A1 - Kamlage, Stefan A1 - Sefkow, Michael A1 - Zimmermann, Nicole A1 - Peter, Martin G. T1 - Concise synthesis of (+)-beta-benzyl gamma-butyrolactones from butynediol Y1 - 2002 ER - TY - THES A1 - Derese, Solomon A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - A new isoflavone from stem bark of Millettia dura Y1 - 2003 SN - 1011-3924 ER - TY - THES A1 - Bahrke, Sven A1 - Einarsson, Jon M. A1 - Gislason, Johannes A1 - Haebel, Sophie A1 - Peter-Katalinic, Jasna A1 - Peter, Martin G. T1 - Characterization of chitooligosaccharides by mass spectrometry Y1 - 2003 SN - 82-47-15901-5 ER - TY - JOUR A1 - Eijsink, Vincent G. H. A1 - Synstad, Bjoenar A1 - Gaseidnes, Sigrid A1 - Komander, David A1 - Houston, Douglas R. A1 - Peter, Martin G. A1 - van Aalten, Daan M. F. T1 - Structure and function of chitinolytic enzymes N2 - The recent work on a variety of family 18 chitonolytic enzymes has yielded important data concerning the structure, substrate-binding, catalysis, inhibitor-binding and even dynamics. These data have been useful in helping to better understand the roles of various types of chitinases in chitin hydrolysis, to rationally engineer the properties of these enzymes, thus making them more suitable as biocatalysts, and to study and understand the effectiveness of natural and designed chitinase inhibitors, which may be of medical interest. On the other hand, the recent work on ChiB shows that catalysis in family 18 chitinases is a highly complicated process, involving larger parts of the enzyme and dynamics. Thus, despite recent discoveries, there is still a lot more to discover about how these enzyme work. Y1 - 2003 SN - 82-471-5901-5 ER - TY - JOUR A1 - Germer, Antje A1 - Mugge, Clemens A1 - Peter, Martin G. A1 - Rottmann, Antje A1 - Kleinpeter, Erich T1 - Solution- and bound-state conformational study of N,N',N''-triacetyl chitotriose and other analogous potential inhibitors of hevamine: Application of trNOESY and STD NMR spectroscopy N2 - The soln.-state conformations of N,N',N''-triacetyl chitotriose (1) and other potential chitinase inhibitors 2-4 were studied using a combination of NMR spectroscopy (NOESY) and mol. mechanics calcns. Detn. solely of the global energy min. conformation was found to be insufficient for an agreement with the NMR results. An appropriate consistency between the NMR exptl. data and theor. calcns. was only reached by assessing the structures as population-weighted av. conformers based on Boltzmann distributions derived from the calcd. relative energies. Analogies, but also particular differences, between the synthetic compds. 2-4 and the naturally-occurring N,N',N''-triacetyl chitotriose were found. Furthermore, the conformation of compds. 1 and 2 when bound to hevamine was also studied using transferred NOESY expts. and the binding process was found to impart a level of conformational restriction on the ligands. The preferred conformation as detd. for 1 in the bound state to hevamine belonged to one of the conformational families found for the compd. when free in soln., although full characterization of the bound-state conformations was impeded due to severe signal overlap. Satn. transfer difference NMR expts. were also employed to analyze the binding epitopes of the bound compds. We thus detd. that it is mainly the acetyl amido groups of the trisaccharide and the heterocyclic moiety which are in close contact with hevamine. Y1 - 2003 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Irungu, Beatrice A1 - Derese, Solomon A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Two prenylated flavonoids from the stem bark of Erythrina burttii N2 - From the stem bark of Erythrina burttii, a new isoflavone, 5,2',4'-trihydroxy-7-methoxy-6-(3- methylbut-2-enyl)isoflavone (trivial name, 7-O-methylluteone) and a new flavanone, 5,7-dihydroxy-4'-methoxy- 3'-(3-methylbutadienyl)-5'-(3-methylbut-2-enyl)flavanone (trivial name, burttinonedehydrate) along with three known isoflavonoids (8-prenylluteone, 3-O-methylcalopocarpin and genistein) were isolated. The structures were detd. on the basis of spectroscopic evidence. Y1 - 2003 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Induli, M. A1 - Derese, Solomon A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Peter, Martin G. A1 - Akala, Hoseah M. A1 - Wangui, Julia A1 - Liyala, Pamela A1 - Waters, Norman C. T1 - Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica N2 - The ethyl acetate extract of the stem bark of Erythrina abyssinica showed anti-plasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 7.9 +/- 1.1 and 5.3 +/- 0.7 mug/ml, respectively. From this extract, a new chalcone, 2,3,4,4'-tetrahydroxy-5- prenylchalcone (trivial name 5-prenylbutein) and a new flavanone, 4',7-dihydroxy-3'-methoxy-5'- prenylflavanone (trivial name, 5-deoxyabyssinin II) along with known flavonoids have been isolated as the anti- plasmodial principles. The structures were determined on the basis of spectroscopic evidence. (C) 2004 Elsevier Ltd. All rights reserved Y1 - 2004 SN - 0031-9422 ER - TY - JOUR A1 - Vaaje-Kolstad, G. A1 - Vasella, A. A1 - Peter, Martin G. A1 - Netter, C. A1 - Houston, Douglas R. A1 - Westereng, B. A1 - Synstad, Bjoenar A1 - Eijsink, Vincent G. H. A1 - van Aalten, Daan M. F. T1 - Interactions of a family 18 chitinase with the designed inhibitor HM508 and its degradation product, chitobiono- delta-lactone N2 - We describe enzymological and structural analyses of the interaction between the family 18 chitinase ChiB from Serratia marcescens and the designed inhibitor N,N'-diacetylchitobionoxime-N-phenylcarbamate (HM508). HM508 acts as a competitive inhibitor of this enzyme with a K-i in the 50 muM range. Active site mutants of ChiB show K-i values ranging from 1 to 200 muM, providing insight into some of the interactions that determine inhibitor affinity. Interestingly, the wild type enzyme slowly degrades HM508, but the inhibitor is essentially stable in the presence of the moderately active D142N mutant of ChiB. The crystal structure of the D142N-HM508 complex revealed that the two sugar moieties bind to the -2 and -1 subsites, whereas the phenyl group interacts with aromatic side chains that line the +1 and +2 subsites. Enzymatic degradation of HM508, as well as a Trp-->Ala mutation in the +2 subsite of ChiB, led to reduced affinity for the inhibitor, showing that interactions between the phenyl group and the enzyme contribute to binding. Interestingly, a complex of enzymatically degraded HM508 with the wild type enzyme showed a chitobiono-delta- lactone bound in the -2 and -1 subsites, despite the fact that the equilibrium between the lactone and the hydroxy acid forms in solution lies far toward the latter. This shows that the active site preferentially binds the E-4 conformation of the -1 sugar, which resembles the proposed transition state of the reaction Y1 - 2004 SN - 0021-9258 ER - TY - JOUR A1 - Berth, Gisela A1 - Dautzenberg, Herbert A1 - Peter, Martin G. T1 - Physica-chemical characterization of chitosans in dilute solution Y1 - 1998 SN - 2-907922-57-2 ER - TY - JOUR A1 - Fotie, J. A1 - Nkengfack, A. E. A1 - Peter, Martin G. A1 - Heydenreich, Matthias A1 - Fomum, Z. T. T1 - Chemical constituents of the ethyl acetate extracts of the stem bark and fruits of Dichrostachys cinerea and the roots of Parkia bicolor N2 - The antibacterial activities of ethyl acetate, methanol and aqueous extracts of the stem bark of Dichrostachys cinerea and the roots of Parkia bicolor have been evaluated. Ethyl acetate extracts have been investigated, studies that led to a series of known compounds, amongst which many are reported here for the very first time from both the species Y1 - 2004 SN - 1011-3924 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Mushibe, E. K. A1 - Induli, M. A1 - Derese, Solomon A1 - Midiwo, Jacob O. A1 - Kabaru, Jacques M. A1 - Heydenreich, Matthias A1 - Koch, Andreas A1 - Peter, Martin G. T1 - 7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoloata N2 - From the acetone extract of the roots of Derris trifoliata an isollavonoid derivative, named 7a-O- methyldeguelol, a modified rotenoid with an open ring-C, representing a new sub-class of isollavonoids (the sub-class is here named as rotenoloid), was isolated and characterised. In addition, the known rotenoids, rotenone, deguelin and alpha-toxicarol, were identified. The structures were determined on the basis of spectroscopic evidence. Rotenone and deguelin were identified as the larvicidal principles of the acetone extract of the roots of Derris trifoliata. (c) 2005 Elsevier Ltd. All rights reserved Y1 - 2005 SN - 0031-9422 ER - TY - JOUR A1 - Yenesew, Abiy A1 - Derese, Solomon A1 - Midiwo, Jacob O. A1 - Bii, Christine C. A1 - Heydenreich, Matthias A1 - Peter, Martin G. T1 - Antimicrobial flavonoids from the stem bark of Erythrina burttii N2 - The chloroform extract of the stem bark of Erythrina burttii showed antifungal and antibacterial activities using the disk diffusion method. Flavonoids were identified as the active principles. Activities were observed against fungi and Gram(+) bacteria, but the Gram(-) bacteria Escherichia coli was resistant. (c) 2005 Elsevier B.V. All rights reserved Y1 - 2005 SN - 0367-326X ER - TY - JOUR A1 - Wanjohi, John M. A1 - Yenesew, Abiy A1 - Midiwo, Jacob O. A1 - Heydenreich, Matthias A1 - Peter, Martin G. A1 - Dreyer, M. A1 - Reichert, M. A1 - Bringmann, Gerhard T1 - Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica N2 - From the fruits of Bulbine abyssinica three new dimeric anthracene derivatives, (P)-8,9,1',8'- tetrahydroxy-3,3'-dimethyl[10,7'-bianthracene]-1,4,9',10'- tetraone (trivial name abyquinone A), (10R)-1,4,8,1',8-pentahydroxy-3,3'-dimethyl-[10,7'-bianthracene]9,9',10' (10H)-trione (trivial name abyquinone B), and (10R)-3,4'-dihydro-1,4,8,3',8',9'-hexahydroxy-3,3'- dimethyl-[10,7'-biant hracene]9,1'(10H,2'H)-dione (trivial name abyquinone Q were isolated. Despite their structural differences, these three compounds are connected to each other by the apparently biomimetic conversion of abyquinone C (a preanthraquinonylanthrone with two stereogenic centers) into B (an anthraquinonylanthrone with one stereogenic center) and finally into A (an axially chiral bianthraquinone) under mild conditions, involving a highly efficient center-to-axis chirality transfer. In addition, the known anthraquinones islandicin and chrysophanol were identified. The structures were determined on the basis of spectroscopical evidences, chemical transformations, and quantum chemical CD calculations. (C) 2005 Elsevier Ltd. All rights reserved Y1 - 2005 SN - 0040-4020 ER - TY - JOUR A1 - Rusu, Viorel Marin A1 - Ng, C. H. A1 - Wilke, Max A1 - Tiersch, Brigitte A1 - Fratzl, Peter A1 - Peter, Martin G. T1 - Size-controlled hydroxyapatite nanoparticles as self-organized organic-in organic composite materials N2 - This paper presents some results concerning the size-controlled hydroxyapatite nanoparticles obtained in aqueous media in a biopolymer matrix from soluble precursors salts. Taking the inspiration from nature, where composite materials made of a polymer matrix and inorganic fillers are often found, e.g. bone, shell of crustaceans, shell of eggs, etc., the feasibility on making composite materials containing chitosan and nanosized hydroxyapatite was investigated. A stepwise co-precipitation approach was used to obtain different types of composites by means of different ratio between components. The synthesis of hydroxyapatite was carried out in the chitosan matrix from calcium chloride and sodium dihydrogenphosphate in alkaline solutions at moderate pH of 10-11 for 24 h. Our research is focused on studying and understanding the structure of this class of composites, aiming at the development of novel materials, controlled at the nanolevel scale. The X-ray diffraction technique was employed in order to study the kinetic of hydroxyapatite formation in the chitosan matrix as well as to determine the HAp crystallite sizes in the composite samples. The hydroxyapatite synthesized using this route was found to be nano-sized (15-50nm). Moreover, applying an original approach to analyze the (002) XRD diffraction peak profile of hydroxyapatite by using a sum of two Gauss functions, the bimodal distribution of nanosized hydroxyapatite within the chitosan matrix was revealed. Two types of size distribution domains such as cluster-like (between 200 and 400 nm), which are the habitat of "small" hydroxyapatite nanocrystallites and scattered-like, which are the habitat of "large" hydroxyapatite nanocrystallites was probed by TEM and CSLM. The structural features of composites suggest that self-assembly processes might be involved. The composites contain nanosized hydroxyapatite with structural features close to those of biological apatites that make them attractive for bone tissue engineering applications. (c) 2005 Elsevier Ltd. All rights reserved Y1 - 2005 SN - 0142-9612 ER - TY - JOUR A1 - Alarcon, Julio A1 - Alderete, Joel B. A1 - Aguila, Sergio A1 - Peter, Martin G. T1 - Regio and stereoselective hydroxylation of alpha-agarofuran by biotransformation of rhizopus nigricans N2 - A new synthesis of 9 alpha-hydroxy-alpha-agarofuran (6 alpha) is described, using a microbiological hydroxylation alpha-agarofuran (5) as the key reaction. The stereochemistry of the biohydroxylation was determined on the basis of a NOESY-experiment and GIAO calculations at the B3LYP/cc-pVDZ level. A strong gamma-effect was observed at C15 of the agarofuran ring which was correctly predicted by the GIAO-B3LYP calculations Y1 - 2005 ER - TY - JOUR A1 - Peikow, Dirk A1 - Matern, Christa-Maria A1 - Peter, Martin G. A1 - Schilde, Uwe T1 - Crystal structure of (1,4,7,10,13-pentaoxacyclopentadecane-O,O ',O '',O ''')(trifluoromethanesulfonato-O,O ')sodium, Na(C10H20O5)(CF3SO3) N2 - C11H20F3NaO8S, monoclinic, P121/nil (no. 11), a = 7.947(1) angstrom, b = 12.056(1) angstrom, c = 9.083(1) angstrom, P = 106.01 (1)degrees, V = 836.4 angstrom(3), Z = 2, R-gt(F) = 0.043, wR(ref)(F-2) = 0.120, T = 210 K. Y1 - 2005 ER -