TY  - JOUR
A1  - Couturier, Jean-Philippe
A1  - Wischerhoff, Erik
A1  - Bernin, Robert
A1  - Hettrich, Cornelia
A1  - Koetz, Joachim
A1  - Sutterlin, Martin
A1  - Tiersch, Brigitte
A1  - Laschewsky, Andre
T1  - Thermoresponsive Polymers and Inverse Opal Hydrogels for the Detection of Diols
JF  - Langmuir
N2  - Responsive inverse opal hydrogels functionalized by boroxole moieties were synthesized and explored as sensor platforms for various low molar mass as well as polymeric diols and polyols, including saccharides, glycopolymers and catechols, by exploiting the diol induced modulation of their structural color. The underlying thermoresponsive water-soluble copolymers and hydrogels exhibit a coil-to-globule or volume phase transition, respectively, of the LCST-type. They were prepared from oligoethylene oxide methacrylate (macro)monomers and functionalized via copolymerization to bear benzoboroxole moieties. The resulting copolymers represent weak polyacids, which can bind specifically to diols within an appropriate pH window. Due to the resulting modulation of the overall hydrophilicity of the systems and the consequent shift of their phase transition temperature, the usefulness of such systems for indicating the presence of catechols, saccharides, and glycopolymers was studied, exploiting the diol/polyol induced shifts of the soluble polymers’ cloud point, or the induced changes of the hydrogels’ swelling. In particular, the increased acidity of benzoboroxoles compared to standard phenylboronic acids allowed performing the studies in PBS buffer (phosphate buffered saline) at the physiologically relevant pH of 7.4. The inverse opals constructed of these thermo- and analyte-responsive hydrogels enabled following the binding of specific diols by the induced shift of the optical stop band. Their highly porous structure enabled the facile and specific optical detection of not only low molar mass but also of high molar mass diol/polyol analytes such as glycopolymers. Accordingly, such thermoresponsive inverse opal systems functionalized with recognition units represent attractive and promising platforms for the facile sensing of even rather big analytes by simple optical means, or even by the bare eye.
Y1  - 2016
U6  - https://doi.org/10.1021/acs.langmuir.6b00803
SN  - 0743-7463
VL  - 32
SP  - 4333
EP  - 4345
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Pavashe, Prashant
A1  - Elamparuthi, Elangovan
A1  - Hettrich, Cornelia
A1  - Moeller, Heiko M.
A1  - Linker, Torsten
T1  - Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A
JF  - The journal of organic chemistry
N2  - A convenient and general synthesis of 2-thiocarbohydrates via cerium ammonium nitrate oxidation of the thiocyanate ion is described. Radical addition to glycals proceeds with excellent regio- and good stereoselectivities in only one step, deprotection affords water-soluble 2-thio saccharides. Binding studies to Con A have been performed by isothermal titration calorimetry (ITC) and saturation transfer difference (STD) NMR spectroscopy. The 2-thiomannose derivative binds even stronger to Con A than the natural substrate, offering opportunities for new lectin or enzyme inhibitors.
Y1  - 2016
U6  - https://doi.org/10.1021/acs.joc.6b00987
SN  - 0022-3263
VL  - 81
SP  - 8595
EP  - 8603
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - GEN
A1  - Wessig, Pablo
A1  - Bader, Denise
A1  - Klier, Dennis Tobias
A1  - Hettrich, Cornelia
A1  - Bier, Frank Fabian
T1  - Detecting carbohydrate–lectin interactions using a fluorescent probe based on DBD dyes
N2  - Herein we present an efficient synthesis of a biomimetic probe with modular construction that can be specifically bound by the mannose binding FimH protein – a surface adhesion protein of E. coli bacteria. The synthesis combines the new and interesting DBD dye with the carbohydrate ligand mannose via a Click reaction. We demonstrate the binding to E. coli bacteria over a large concentration range and also present some special characteristics of those molecules that are of particular interest for the application as a biosensor. In particular, the mix-and-measure ability and the very good photo-stability should be highlighted here.
T3  - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - 314 
KW  - conformational-changes
KW  - green-i
KW  - protein
KW  - binding
KW  - assay
Y1  - 2016
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus4-394382
SP  - 1235
EP  - 1238
ER  -