title: Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-O-tetradecanoyl-α-d-cholesterylglycosides.
abstract: A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66-78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling.
authors.affiliation: Department of Chemistry, University of California, Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Davis
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D000215:Acylation; D002240:Carbohydrate Sequence; D002788:Cholesterol Esters / Q000737:chemistry*; D005690:Galactose / Q000138:chemical synthesis / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D007454:Iodides / Q000737:chemistry*
chemical_list: D002788:Cholesterol Esters; D006017:Glycolipids; D007454:Iodides; D005690:Galactose
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