Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-o-tetradecanoyl-α- d -cholesterylglycosides

Ryan A. Davis, James C. Fettinger, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

10 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)8447-8452
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number17
DOIs
StatePublished - Sep 5 2014

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Glycosylation
Acylation
Iodides
Galactose
Sugars
Esters

ASJC Scopus subject areas

  • Organic Chemistry

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Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-o-tetradecanoyl-α- d -cholesterylglycosides. / Davis, Ryan A.; Fettinger, James C.; Gervay-Hague, Jacquelyn.

In: Journal of Organic Chemistry, Vol. 79, No. 17, 05.09.2014, p. 8447-8452.

Research output: Contribution to journalArticle

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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.",
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