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Issue 41, 2014
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A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities

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Abstract

An efficient 2′-O- to 3′-C-β-D-glucosidic bond rearrangement on the dihydrochalcone phloretin to convert phlorizin into nothofagin was achieved by combining complementary O-glycosyltransferase (OGT) and C-glycosyltransferase (CGT) activities in a one-pot transformation containing catalytic amounts of uridine 5′-diphosphate (UDP). Two separate enzymes or a single engineered dual-specific O/CGT were applied. Overall (quantitative) conversion occurred in two steps via intermediary UDP–glucose and phloretin.

Graphical abstract: A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities

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Publication details

The article was received on 21 Jan 2014, accepted on 19 Mar 2014 and first published on 25 Mar 2014


Article type: Communication
DOI: 10.1039/C4CC00536H
Citation: Chem. Commun., 2014,50, 5465-5468
  • Open access: Creative Commons BY-NC license
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    A two-step O- to C-glycosidic bond rearrangement using complementary glycosyltransferase activities

    A. Gutmann, C. Krump, L. Bungaruang and B. Nidetzky, Chem. Commun., 2014, 50, 5465
    DOI: 10.1039/C4CC00536H

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