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Issue 72, 2012
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Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori

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Abstract

In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation–deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified quantities available to the biological community for the first time.

Graphical abstract: Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori

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Publication details

The article was received on 01 Jun 2012, accepted on 18 Jul 2012 and first published on 02 Aug 2012


Article type: Communication
DOI: 10.1039/C2CC33948J
Citation: Chem. Commun., 2012,48, 9083-9085
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    Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori

    R. A. Davis, C. Lin and J. Gervay-Hague, Chem. Commun., 2012, 48, 9083
    DOI: 10.1039/C2CC33948J

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