Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form
As of April 1st VIVO Scientific Profiles will no longer updated for faculty, and the link to VIVO will be removed from the library website. Faculty profile pages will continue to be updated via Interfolio. VIVO will continue being used behind the scenes to update graduate student profiles. Please contact helplib@scripps.edu if you have questions.
How to download citations from VIVO | Alternative profile options

Alpha-glycosylation by d-glucosamine-derived donors: Synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

authors

  • Zulueta, M. M. L.
  • Lin, S. Y.
  • Lin, Y. T.
  • Huang, C. J.
  • Wang, C. C.
  • Ku, C. C.
  • Shi, Z. H.
  • Chyan, C. L.
  • Irene, D.
  • Lim, L. H.
  • Tsai, T. I.
  • Hu, Y. P.
  • Arco, S. D.
  • Wong, Chi-Huey
  • Hung, S. C.

publication date

  • May 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Numerous biomolecules possess ?-D-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted ?-isomer. We report herein a versatile approach in affording full ?-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.
  • 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.

subject areas

  • Disaccharides
  • Glucosamine
  • Glycosylation
  • Heparin
  • Lectins
  • Mycobacterium tuberculosis
  • Peptide Fragments
  • Stereoisomerism
  • Substrate Specificity
scroll to property group menus

Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja302640p

PubMed ID

  • 22587381
scroll to property group menus

Additional Document Info

start page

  • 8988

end page

  • 8995

volume

  • 134

issue

  • 21

©2022 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support