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 Polt

doi:10.1016/j.carres.2012.01.008

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 Polt

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

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 language	English (US)
Pages (from-to)	121-125
Number of pages	5
Journal	Carbohydrate Research
Volume	351
DOIs	https://doi.org/10.1016/j.carres.2012.01.008
State	Published - Apr 1 2012

Keywords

Glycosylation
Indium tribromide
O-linked glycopeptides
Serine
Threonine

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/j.carres.2012.01.008

Cite this

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

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.",

keywords = "Glycosylation, Indium tribromide, O-linked glycopeptides, Serine, Threonine",

author = "Lefever, \{Mark R.\} and Szab, \{Lajos Z.\} and Bobbi Anglin and Michael Ferracane and Joanna Hogan and Lauren Cooney and Robin Polt",

note = "Funding Information: We thank the Office of Naval Research (N00014-05-1-0807 \& N00014-02-1-0471), the National Science Foundation (CHE-607917) and the National Institutes of Health (NINDS-NS-052727) for Support. ",

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doi = "10.1016/j.carres.2012.01.008",

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T1 - Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids

AU - Lefever, Mark R.

AU - Szab, Lajos Z.

AU - Anglin, Bobbi

AU - Ferracane, Michael

AU - Hogan, Joanna

AU - Cooney, Lauren

AU - Polt, Robin

N1 - Funding Information: We thank the Office of Naval Research (N00014-05-1-0807 & N00014-02-1-0471), the National Science Foundation (CHE-607917) and the National Institutes of Health (NINDS-NS-052727) for Support.

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N2 - 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.

AB - 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.

KW - Glycosylation

KW - Indium tribromide

KW - O-linked glycopeptides

KW - Serine

KW - Threonine

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