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

Author(s)

Oleg Bol'shakov, University of Florida
Judit K. Beagle, University of DaytonFollow
Mamta Chahar, University of Florida
Khanh Ha, University of Florida
Levan Khelashvili, University of Florida
Alan R. Katritzky, University of Florida

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.

Copyright

Copyright © 2012, European Peptide Society and John Wiley & Sons

Publisher

John Wiley & Sons

Volume

18

Peer Reviewed

yes

Issue

11

eCommons Citation

Bol'shakov, Oleg; Beagle, Judit K.; Chahar, Mamta; Ha, Khanh; Khelashvili, Levan; and Katritzky, Alan R., "S- to N-Acyl Transfer in S-Acylcysteine Isopeptides via 9-, 10-, 12-, and 13-Membered Cyclic Transition States" (2012). Chemistry Faculty Publications. 71.
https://ecommons.udayton.edu/chm_fac_pub/71