title: Glycosylation of α-amino acids by sugar acetate donors with InBr3. 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.
authors.affiliation: Carl S. Marvel Laboratories, Department of Chemistry & Biochemistry, The University of Arizona, Tucson, AZ 85721, USA.
authors.forename: Mark R
authors.initials: MR
authors.lastname: Lefever
authors.forename: Lajos Z
authors.initials: LZ
authors.lastname: Szabò
authors.forename: Bobbi
authors.initials: B
authors.lastname: Anglin
authors.forename: Michael
authors.initials: M
authors.lastname: Ferracane
authors.forename: Joanna
authors.initials: J
authors.lastname: Hogan
authors.forename: Lauren
authors.initials: L
authors.lastname: Cooney
authors.forename: Robin
authors.initials: R
authors.lastname: Polt
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D006031:Glycosylation; D007204:Indium / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*
chemical_list: D000085:Acetates; D000596:Amino Acids; D058116:Lewis Acids; C530781:indium bromide; D007204:Indium