title: Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori.
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.
authors.affiliation: Department of Chemistry, University of California Davis, One Shields Avenue, Davis, CA 95616, USA.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Davis
authors.forename: Chun-Hung
authors.initials: CH
authors.lastname: Lin
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D001692:Biological Transport; D060326:Chemistry Techniques, Synthetic; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins / Q000378:metabolism*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D016480:Helicobacter pylori / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D005656:Fungal Proteins; D006017:Glycolipids; D012503:Saponins; C027578:cholesteryl glucoside; D002784:Cholesterol; D008049:Lipase; C431349:lipase B, Candida antarctica