Abstract
Abstract To better understand acyl transfer reactions of oligopeptides, seventeen N -acyl amino acid esters were solvolyzed in mildly basic methanol- d 4 . All show pseudo-first-order kinetics by 1 H NMR. The rate constant varies up to 400-fold with the identity of the amino acid and up to 6200-fold with the identity of the N -acyl group. The impact of the N -acyl group on the rate constant is discussed in terms of crowding, amide conformation, and amide C O bond character.
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