Title

S- to N-Acyl Transfer in S-Acylcysteine Isopeptides via 9-, 10-, 12-, and 13-Membered Cyclic Transition States

Document Type

Article

Publication Date

11-2012

Publication Source

Journal of Peptide Science

Abstract

S-Acyl cysteine peptides containing α-, β- or γ-amino acid residues undergo long-range S- to N-acyl transfer to give analogs of native tripeptides and tetrapeptides containing additional carbon atoms in the chain. The ease of intramolecular S → N-acyl transfer relative to intermolecular transacylation is favored increasingly for 9 < 12 < 13 ~ 10-membered cyclic transition states; the observed order is explained on conformational and intermolecular interaction considerations.

Inclusive pages

704–709

ISBN/ISSN

1075-2617

Comments

Permission documentation is on file.

Publisher

John Wiley & Sons

Volume

18

Issue

11

Peer Reviewed

yes