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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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Publication details

The article was received on 21 Mar 2016, accepted on 04 May 2016 and first published on 04 May 2016


Article type: Paper
DOI: 10.1039/C6OB00608F
Citation: Org. Biomol. Chem., 2016,14, 4859-4864
  • Open access: Creative Commons BY-NC license
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    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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