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Long-Range Intramolecular S -> N Acyl Migration: A Study of the Formation of Native Peptide Analogues via 13-, 15-, and 16-Membered Cyclic Transition States
Journal article   Peer reviewed

Long-Range Intramolecular S -> N Acyl Migration: A Study of the Formation of Native Peptide Analogues via 13-, 15-, and 16-Membered Cyclic Transition States

Khanh Ha, Mamta Chahar, Jean-Christophe M. Monbaliu, Ekaterina Todadze, Finn K. Hansen, Alexander A. Oliferenko, Charles E. Ocampo, David Leino, Aaron Lillicotch, Christian V. Stevens, …
Journal of organic chemistry, Vol.77(6), pp.2637-2648
16/03/2012
DOI: https://doi.org/10.1021/jo2023125
PMID: 22283871

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
The intramolecular long-range S -> N acyl migration via 13-, 15-, and 16-membered cyclic transition states to form native tetra- and pentapeptide analogues was studied on S-acylcysteine peptides containing beta- or gamma-amino acids. The pH-dependency study of the acyl migration via a 15-membered cyclic transition state indicated that the reaction is favored at a pH range from 7.0 to 7.6. Experimental observations are supported by structural and computational investigations.

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