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

Gao-Lan Zhang; Madhusudhan Reddy Gadi; Xikai Cui; Ding Liu; Jiabin Zhang; Varma Saikam; Christopher Gibbons; Peng G. Wang; Lei Li

doi:10.1039/D1GC00098E

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Gao-Lan Zhang,‡^a Madhusudhan Reddy Gadi,

‡*^a Xikai Cui,^a Ding Liu,^a Jiabin Zhang,^a Varma Saikam,

^a Christopher Gibbons,^a Peng G. Wang §^a and Lei Li

*^a

Author affiliations

* 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.

This article is part of the themed collection: 2021 Green Chemistry Hot Articles

Download options Please wait...

Associated articles

Correction: Protecting-group-free S-glycosylation towards thioglycosides and thi…

Supplementary files

Supplementary information PDF (3269K)

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

Download Citation

Green Chem., 2021,23, 2907-2912

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Green Chemistry

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

Abstract

Associated articles

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements