53029
2018
2018
eng
8
8
article
Nature Publ. Group
London
1
2018-04-26
2018-04-26
--
Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)
Sugar amino acids (SAAs), as biologically interesting structures bearing both amino and carboxylic acid functional groups represent an important class of multifunctional building blocks. In this study, we develop an easy access to novel SAAs in only three steps starting from nitro compounds in high yields in analytically pure form, easily available by ceric (IV) mediated radical additions. Such novel SAAs have been applied in the assembly of total nine carbopeptoids with the form of linear homo-and heterooligomers for the structural investigations employing circular dichroism (CD) spectroscopy, which suggest that the carbopeptoids emerge a well-extended, left (or right)-handed conformation similar to polyproline II (PPII) helices. NMR studies also clearly demonstrated the presence of ordered secondary structural elements. 2D-ROESY spectra were acquired to identify i+1NH <-> (C1H)-C-i, (C2H)-C-i correlations which support the conformational analysis of tetramers by CD spectroscopy. These findings provide interesting information of SAAs and their oligomers as potential scaffolds for discovering new drugs and materials.
Scientific reports
10.1038/s41598-018-24927-6
29700416
2045-2322
wos:2018
6625
WOS:000430919900074
Yin, J (reprint author), Jiangnan Univ, Sch Biotechnol, Key Lab Carbohydrate Chem & Biotechnol, Minist Educ, Lihu Ave 1800, Wuxi 214122, Jiangsu, Peoples R China.; Hu, J (reprint author), Jiangnan Univ, Wuxi Sch Med, Lihu Ave 1800, Wuxi 214122, Jiangsu, Peoples R China., hujing@jiangnan.edu.cn; jianyin@jiangnan.edu.cn
National Natural Science Foundation of ChinaNational Natural Science Foundation of China [21302068, 21502071]; Natural Science Foundation of Jiangsu ProvinceJiangsu Planned Projects for Postdoctoral Research FundsNatural Science Foundation of Jiangsu Province [BK20150154]; Fundamental Research Funds for the Central UniversitiesFundamental Research Funds for the Central Universities [JUSRP51712B]; Public Health Research Center at Jiangnan University [JUPH201502]; Max Planck Society International Partner Group Program; High-end Foreign Experts Recruitment Program; Thousand Talents Plan (Young Professionals); China Scholarship CouncilChina Scholarship Council
2021-12-08T09:37:58+00:00
sword
importub
filename=package.tar
913c29e177edce9dad7fe63cc7e13c8a
Hu, Jing
Yin, Jian
false
true
CC-BY - Namensnennung 4.0 International
Guang-Zong Tian
Jing Hu
Heng-Xi Zhang
Christoph Rademacher
Xiao-Peng Zou
Hong-Ning Zheng
Fei Xu
Xiao-Li Wang
Torsten Linker
Jian Yin
Chemie und zugeordnete Wissenschaften
Institut für Chemie
Import
38748
2015
2015
zho
699
704
6
7
73
article
Science China Press
Beijing
1
--
--
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Study on the Synthesis of Novel Sugar Amino Acids
新型糖氨基酸类化合物的合成研究
Sugar amino acids (SAAs) are carbohydrate derivatives bearing both amino and carboxylic acid functional groups. SAAs represent an important class of multifunctional building blocks, which are amenable to serve as glycomimetics or peptidomimetics with well-defined structures and useful properties. Because SAAs exist in nature in many forms with various biological activities, recently, many unnatural SAAs, as the demand for finding new molecules to discover new drugs and new materials, have been designed and synthesized by a number of research groups. In this paper, we have developed a convenient method for the synthesis of novel SAAs gluco-7 and galacto-7 for the first time. The structure of gluco-7 was similar to the natural SAA glucosaminuronic acid that was a component of many typical bacterial cell walls and could be used for the preparation of type D flu vaccine; while galacto-7 was similar to the natural SAA galactosaminuronic acid that was one of bacterial Vi-antigen components of Escherichia coli. Starting from unexpensive and commercially available 3,4,6-tri-O-acetyl-D-glucal and 3,4,6-tri-O-acetyl-D-galactal, two novel SAAs gluco-7 and galacto-7 were achieved in the linear 6 steps with 34% overall yield and 19% overall yield, respectively. The key reactions included radical addition, decarboxylation, iodine generation reaction, azide reaction and reductive amination reaction. The crucial step was the synthesis of the target compound gluco-7 from gluco-6. By using method A, the target compound gluco-7 was obtained in 4 steps with 63% overall yield. To optimize the transformation from gluco-6 to gluco-7, method B was developed to generate gluco-7 by using one-pot reaction successfully with 76% yield only in one step. It proved that method B was superior to method A with shorter steps and higher yields. All the new compounds were characterized by IR, H-1 NMR, C-13 NMR and HRMS data. Study on the synthesis and biological evaluation of linear and cyclic oligomers derived from gluco-7 and galacto-7 are currently in progress.
Acta chimica Sinica = Huaxue-xuebao
10.6023/A15030205
0567-7351
wos:2015
WOS:000360199200006
Wang, XB (reprint author), Jiangnan Univ, Sch Biotechnol, Minist Educ, Key Lab Carbohydrate Chem & Biotechnol, Lihu Ave 1800, Wuxi 214122, Jiangsu, Peoples R China., jianyin@jiangnan.edu.cn
National Science Foundation for Young Scientists of China [21302068]; Natural Science Foundation of Jiangsu Province, China [BK20130127]; specialized Research Fund for the Doctoral Program of Higher Education [20120093120002]; Fundamental Research Funds for the Central Universities [JUSRP51319B, JUSRP51411B]
Xuebin Wang
Xiaoli Wang
Jing Hu
Zhaoya Wang
Tukaram M. Pimpalpalle
Torsten Linker
Jian Yin
eng
uncontrolled
sugar amino acids
eng
uncontrolled
glycal
eng
uncontrolled
radical addition
eng
uncontrolled
one-pot reaction
eng
uncontrolled
synthesis
Institut für Chemie
Referiert