Regioselective oxidation of unprotected 1,4 linked glucans

作者：Eisink Niek N H M; Lohse Jonas; Witte Martin D^*; Minnaard Adriaan J^*

来源：Organic and Biomolecular Chemistry, 2016, 14(21): 4859-4864.

DOI：10.1039/c6ob00608f

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.

• 出版日期2016-6-7