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Structure dependence in the solvolysis kinetics of amino acid esters

✍ Scribed by John Haseltine; Jason W. Runyon

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 190 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.04.063

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✦ Synopsis

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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