Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
J Org Chem. 2012 Mar 16;77(6):2637-48. doi: 10.1021/jo2023125. Epub 2012 Feb 28.
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 β- or γ-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.
本研究通过β-或γ-氨基酸的 S-酰基半胱氨酸肽，对通过 13、15 和 16 元环过渡态进行的分子内长程 S→N 酰基迁移，以形成天然四肽和五肽类似物进行了研究。通过 15 元环过渡态的酰基迁移的 pH 值依赖性研究表明，该反应在 pH 值为 7.0 至 7.6 的范围内有利于进行。实验观察结果得到了结构和计算研究的支持。
