Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 6, Pages 2637-2648Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2023125
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- Belgian American Educational Foundation, Inc. (B.A.E.F.)
- Research Foundation-Flanders (FWO-Vlaanderen, Belgium)
- Kenan Foundation (University of Florida)
- King Abdulaziz University (Saudi Arabia)
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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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