Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids

Mark R. Lefever, Lajos Z. Szab, Bobbi Anglin, Michael Ferracane, Joanna Hogan, Lauren Cooney, Robin L Polt

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr 3 promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

Original languageEnglish (US)
Pages (from-to)121-125
Number of pages5
JournalCarbohydrate Research
Volume351
DOIs
StatePublished - Apr 1 2012

Fingerprint

Amino Sugars
Glycosylation
Lewis Acids
Glycosides
Sugars
Acetates
Amino Acids
Glycopeptides
Threonine
Serine
Chemical activation

Keywords

  • Glycosylation
  • Indium tribromide
  • O-linked glycopeptides
  • Serine
  • Threonine

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids. / Lefever, Mark R.; Szab, Lajos Z.; Anglin, Bobbi; Ferracane, Michael; Hogan, Joanna; Cooney, Lauren; Polt, Robin L.

In: Carbohydrate Research, Vol. 351, 01.04.2012, p. 121-125.

Research output: Contribution to journalArticle

Lefever, Mark R. ; Szab, Lajos Z. ; Anglin, Bobbi ; Ferracane, Michael ; Hogan, Joanna ; Cooney, Lauren ; Polt, Robin L. / Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids. In: Carbohydrate Research. 2012 ; Vol. 351. pp. 121-125.
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AU - Cooney, Lauren

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