Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-?-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori.
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ABSTRACT:
SUBMITTER: Davis RA
PROVIDER: S-EPMC4271795 | biostudies-literature | 2012 Sep
REPOSITORIES: biostudies-literature
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Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori.
Davis Ryan A RA Lin Chun-Hung CH Gervay-Hague Jacquelyn J
Chemical communications (Cambridge, England) 20120802 72
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. ...[more]
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