S‐ to N‐Acyl transfer in S‐acylcysteine isopeptides via 9‐, 10‐, 12‐, and 13‐membered cyclic transition states |
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| Authors: | Oleg Bol'shakov Judit Kovacs Mamta Chahar Khanh Ha Levan Khelashvili Alan R Katritzky |
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| Institution: | 1. Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, , Gainesville, FL, 32611‐7200 USA;2. Chemistry Department, King Abdulaziz University, , Jeddah, 21589 Saudi Arabia |
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| 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. Copyright © 2012 European Peptide Society and John Wiley & Sons, Ltd. |
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| Keywords: | S‐ to N‐acyl transfer peptides cysteine N‐acylbenzotriazoles S‐acylation |
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