Issue 21, 2016
From the journal:

Organic & Biomolecular Chemistry

Regioselective oxidation of unprotected 1,4 linked glucans†

Niek N. H. M. Eisink,a   Jonas Lohse,a   Martin D. Witte*a  and  Adriaan J. Minnaard*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands
E-mail: A.J.Minnaard@rug.nl, m.d.witte@rug.nl

Abstract

Palladium-catalyzed alcohol oxidation allows the chemo- and regioselective modification of unprotected 1,4 linked glucans. This is demonstrated in the two-step bisfunctionalization of 1,4 linked glucans up to the 7-mer. Introduction of an anomeric azide is followed by a highly regioselective mono-oxidation of the terminal C3–OH functionality. The resulting orthogonal bis-functionalized oligosaccharides are a viable alternative to PEG-spacers as demonstrated in the conjugation of a cysteine mutant of 4-oxalocrotonate tautomerase with biotin.

Graphical abstract: Regioselective oxidation of unprotected 1,4 linked glucans

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C6OB00608F
Article type
Paper
Submitted
21 Mar 2016
Accepted
04 May 2016
First published
04 May 2016
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2016,14, 4859-4864

Permissions

Request permissions

Regioselective oxidation of unprotected 1,4 linked glucans

N. N. H. M. Eisink, J. Lohse, M. D. Witte and A. J. Minnaard, Org. Biomol. Chem., 2016, 14, 4859 DOI: 10.1039/C6OB00608F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements