Efficient Iterative Synthesis of O-Acetylated Tri- to Pentadecasaccharides Related to the Lipopolysaccharide of Shigella flexneri Type 3 a through Di- and Trisaccharide Glycosyl Donors - Archive ouverte HAL Access content directly
Journal Articles Chemistry - An Asian Journal Year : 2017

Efficient Iterative Synthesis of O-Acetylated Tri- to Pentadecasaccharides Related to the Lipopolysaccharide of Shigella flexneri Type 3 a through Di- and Trisaccharide Glycosyl Donors

(1) , (1, 2) , (1)
1
2

Abstract

Protection against bacterial infections, including shigellosis, can be achieved by antibodies against the bacterial surface polysaccharide. In line with our efforts to develop vaccine candidates for shigellosis, we report herein the synthesis of penta-, deca-, and pentadecasaccharides as well as tri-, octa-, and tridecasaccharides as the endchain and intrachain fragments, respectively, of the surface polysaccharide of Shigella flexneri 3 a, a prevalent serotype. The syntheses relied on the efficiency of the trichloroacetimidate glycosylation chemistry, whereby iteration with di- and trisaccharide building blocks provided fragments made of up to three mono-O-acetylated polysaccharide repeating units. Pd(OH)2 -mediated hydrogenation/hydrogenolysis enabled the concomitant removal or conversion of up to 31 protecting groups of 4 different origins to provide the targets as propyl glycosides. Oligosaccharides comprising the octasaccharide segment were shown to display high conformational similarities in solution.
Not file

Dates and versions

pasteur-01627935 , version 1 (02-11-2017)

Identifiers

Cite

Zhaoyu Hu, Aileen F Bongat White, Laurence A Mulard. Efficient Iterative Synthesis of O-Acetylated Tri- to Pentadecasaccharides Related to the Lipopolysaccharide of Shigella flexneri Type 3 a through Di- and Trisaccharide Glycosyl Donors. Chemistry - An Asian Journal, 2017, 12 (4), pp.419 - 439. ⟨10.1002/asia.201600819⟩. ⟨pasteur-01627935⟩

Collections

PASTEUR CNRS
95 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More