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Issue 21, 2016
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Regioselective oxidation of unprotected 1,4 linked glucans

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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

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Supplementary files

Article information


Submitted
21 Mar 2016
Accepted
04 May 2016
First published
04 May 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 4859-4864
Article type
Paper

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

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