Issue 43, 2022
From the journal:

RSC Advances

A Ferrier glycosylation/cis-dihydroxylation strategy to synthesize Leishmania spp. lipophosphoglycan-associated βGal(1,4)Man disaccharide†

Dipesh Budhathoki,a   Bhavesh Deore, ORCID logo a   M. G. Finnb  and  Carlos A. Sanhueza ORCID logo *ab  

* Corresponding authors

a Department of Pharmaceutical Sciences, St. John's University, 8000 Utopia Parkway, Queens, NY 11439, USA
E-mail: chavezc@stjohns.edu

b School of Chemistry and Biochemistry, Georgia Institute of Technology, 901 Atlantic Drive, Atlanta, GA 30306, USA

Abstract

The Galβ(1→4)Man disaccharide, found in the cell surface lipophosphoglycan (LPG) of Leishmania species, has been synthesized by a Ferrier glycosylation/cis-dihydroxylation strategy. This stereoselective method proved efficient for synthesizing the target saccharide in good yield. In addition, we prepared two clickable O-glycoside and phospho-glycoside versions of Galβ(1→4)Man to enable conjugation to protein carriers for further immunological and antibody-binding studies.

Graphical abstract: A Ferrier glycosylation/cis-dihydroxylation strategy to synthesize Leishmania spp. lipophosphoglycan-associated βGal(1,4)Man disaccharide

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Article information

DOI
https://doi.org/10.1039/D2RA05158C
Article type
Paper
Submitted
17 Aug 2022
Accepted
27 Sep 2022
First published
04 Oct 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 28207-28216

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A Ferrier glycosylation/cis-dihydroxylation strategy to synthesize Leishmania spp. lipophosphoglycan-associated βGal(1,4)Man disaccharide

D. Budhathoki, B. Deore, M. G. Finn and C. A. Sanhueza, RSC Adv., 2022, 12, 28207 DOI: 10.1039/D2RA05158C

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