ArticleChemistryOpen2015
Synthesis of a Glucuronic Acid-Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments.
Article in ChemistryOpen, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Synthetic Glycans Reveal Determinants of Antibody Functional Efficacy against a Fungal Pathogen.ACS infectious diseases · 2024Article
- A glycan FRET assay for detection and characterization of catalytic antibodies to theProceedings of the National Academy of Sciences of the United States of America · 2021Article
- Potential targets for next generation antimicrobial glycoconjugate vaccines.FEMS microbiology reviews · 2018Review
- Synthesis of a Glucuronic Acid-Containing Thioglycoside Trisaccharide Building Block and Its Use in the Assembly of Cryptococcus Neoformans Capsular Polysaccharide Fragments.ChemistryOpen · 2015Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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