A New Oxyma Derivative for Non-racemizable Amide-forming Reactions in Water

摘要

An oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2) displayed remarkable physico-chemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short-to oligo-peptides could be synthesized by using 2, EDCI, and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous work-up procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.