Glycosylation of α-amino acids by sugar acetate donors with InBr3. Minimally competent Lewis acids

Mark R Lefever; Lajos Z Szabò; 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 InBr3. Minimally competent Lewis acids

Carbohydr Res. 2012 Apr 1:351:121-5. doi: 10.1016/j.carres.2012.01.008. Epub 2012 Jan 28.

Authors

Mark R Lefever¹, Lajos Z Szabò, Bobbi Anglin, Michael Ferracane, Joanna Hogan, Lauren Cooney, Robin Polt

Affiliation

¹ Carl S. Marvel Laboratories, Department of Chemistry & Biochemistry, The University of Arizona, Tucson, AZ 85721, USA.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acetates / chemistry*
Amino Acids / chemistry*
Catalysis
Glycosylation
Indium / chemistry*
Lewis Acids / chemistry*

Substances

Acetates
Amino Acids
Lewis Acids
indium bromide
Indium

Abstract

Publication types

MeSH terms

Substances

Grants and funding