Enhanced N-terminal Glycine Modification with Electron Deficient o-Oxyacetate Aromatic Aldehydes

Abstract

N-terminus glycine was selectively converted into aminoalcohols using o-oxyacetate aromatic aldehydes. Three novel analogs were synthesized and enhanced reactivity was observed with molecules bearing electron-withdrawing/pyridyl groups. Computational studies revealed enol formation as rate-limiting step, where reduced electron density lowered α-carbon pKa and energy barriers, aligning with experimental trends.