Divergent behavior of glycosylated threonine and serine derivatives in solid phase peptide synthesis

Article abstract of DOI:10.1021/ol301723e

Solid phase peptide coupling of glycosylated threonine derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo β-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity. This article not subject to U.S. Copyright. Published 2012 by the American Chemical Society.