Issue 8, 2021
From the journal:

Green Chemistry

Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water†

Gao-Lan Zhang,‡a   Madhusudhan Reddy Gadi, ORCID logo ‡*a   Xikai Cui,a   Ding Liu,a   Jiabin Zhang,a   Varma Saikam, ORCID logo a   Christopher Gibbons,a   Peng G. Wang§a  and  Lei Li ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Georgia State University, 50 Decatur ST SE, Atlanta, Georgia, USA
E-mail: mgadi@gsu.edu, lli22@gsu.edu

Abstract

A facile and green S-glycosylation method has been developed featuring protecting-group-free and proceeding-in-water like enzymatic synthesis. Glycosylation of fluoride donors with thiol sugar acceptors using Ca(OH)2 as a promoter afforded various thioglycosides in good yields with exclusive stereoselectivity. This method also enabled the successful production of S-linked oligosaccharides and S-linked glycopeptides.

Graphical abstract: Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water

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Article information

DOI
https://doi.org/10.1039/D1GC00098E
Article type
Communication
Submitted
08 Jan 2021
Accepted
01 Mar 2021
First published
01 Mar 2021

Green Chem., 2021,23, 2907-2912

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Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water

G. Zhang, M. R. Gadi, X. Cui, D. Liu, J. Zhang, V. Saikam, C. Gibbons, P. G. Wang and L. Li, Green Chem., 2021, 23, 2907 DOI: 10.1039/D1GC00098E

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