Open AccessSynthesis of a Glucuronic Acid‐Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments
Author(s) -
Guazzelli Lorenzo,
Ulc Rebecca,
Oscarson Stefan
Publication year - 2015
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201500143
Subject(s) - cryptococcus neoformans , trisaccharide , chemistry , glycosylation , glycan , polysaccharide , glucuronic acid , stereochemistry , biochemistry , glycoprotein , microbiology and biotechnology , biology
As part of an ongoing project aimed at identifying protective capsular polysaccharide epitopes for the development of vaccine candidates against the fungal pathogen Cryptococcus neoformans , the synthesis and glycosylation properties of a naphthalenylmethyl (NAP) orthogonally protected trisaccharide thioglycoside, a common building block for construction of serotype B and C capsular polysaccharide structures, were investigated. Ethyl (benzyl 2,3,4‐tri‐ O ‐benzyl‐β‐ d ‐glucopyranosyl‐ uronate)‐(1→2)‐[2,3,4‐tri‐ O ‐benzyl‐β‐ d ‐xylopyranosyl‐(1→4)]‐6‐ O ‐benzyl‐3‐ O ‐(2‐naphthalenylmethyl)‐1‐thio‐α‐ d ‐mannopyranoside was prepared and used both as a donor and an acceptor in glycosylation reactions to obtain spacer equipped hexa‐ and heptasaccharide structures suitable either for continued elongation or for deprotection and printing onto a glycan array or conjugation to a carrier protein. The glycosylation reactions proceeded with high yields and α‐selectivity, proving the viability of the building block approach also for construction of 4‐ O ‐xylosyl‐containing C. neoformans CPS structures.