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

Ryan A. Davis; Chun Hung Lin; Jacquelyn Gervay-Hague

doi:10.1039/c2cc33948j

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

Ryan A. Davis, Chun Hung Lin, Jacquelyn Gervay-Hague

Chemistry

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

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.

Original language	English (US)
Pages (from-to)	9083-9085
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	72
DOIs	https://doi.org/10.1039/c2cc33948j
State	Published - Sep 18 2012

ASJC Scopus subject areas

Metals and Alloys
Materials Chemistry
Surfaces, Coatings and Films
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Catalysis
Chemistry(all)

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AU - Lin, Chun Hung

AU - Gervay-Hague, Jacquelyn

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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