NDLI: α-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin.

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α-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin.

Content Provider	Semantic Scholar
Author	Zulueta, Medel Manuel L. Lin, Shu-Yi Lin, Ya-Ting Huang, Ching-Jui Wang, Chun-Chih Ku, Chiao-Chu Shi, Zhonghao Chyan, Chia-Lin Irene, Deli Lim, Liang-Hin Tsai, Tsung-I Hu, Yu-Peng Arco, Susan D. Wong, Chi-Huey Hung, Shang-Cheng
Copyright Year	2012
Abstract	Numerous biomolecules possess α-D-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted β-isomer. We report herein a versatile approach in affording full α-stereoselectivity built upon a carefully selected set of orthogonal protecting groups on a D-glucosaminyl donor. The excellent stereoselectivity provided by the protecting group combination was found independent of leaving groups and activators. With the trichloroacetimidate as the optimum donor leaving group, core skeletons of glycosylphosphatidyl inositol anchors, heparosan, heparan sulfate, and heparin were efficiently assembled. The orthogonal protecting groups were successfully manipulated to further carry out the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and octasaccharide analogues. Using the heparin analogues, heparin-binding hemagglutinin, a virulence factor of Mycobacterium tuberculosis, was found to bind at least six sugar units with the interaction notably being entropically driven.
File Format	PDF HTM / HTML
DOI	10.1021/ja302640p
PubMed reference number	22587381
Journal	Medline
Volume Number	134
Issue Number	21
Alternate Webpage(s)	https://ir.nctu.edu.tw/bitstream/11536/16297/1/000304570700043.pdf
Alternate Webpage(s)	https://doi.org/10.1021/ja302640p
Journal	Journal of the American Chemical Society
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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