Issue 72, 2012
From the journal:

Chemical Communications

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

Ryan A. Davis,a   Chun-Hung Linb  and  Jacquelyn Gervay-Hague*a  

* Corresponding authors

a Department of Chemistry, University of California Davis, One Shields Avenue, Davis, CA, USA
E-mail: jgervayhague@ucdavis.edu
Fax: +1 530 754 6915
Tel: +1 530 754 9557

b Institute of Biological Chemistry, Academia Sinica, No. 128 Academia Road Section 2, Nan-Kang, Taipei, Taiwan

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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Article information

DOI
https://doi.org/10.1039/C2CC33948J
Article type
Communication
Submitted
01 Jun 2012
Accepted
18 Jul 2012
First published
02 Aug 2012

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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