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. Enhanced reactivity was observed with aldehydes bearing electron-withdrawing/pyridyl groups. Computational studies revealed enol formation as the rate-limiting step, where reduced electron density lowered the α-carbon pK_a and energy barriers, aligning with experimental trends.