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

被引：29

作者：

Ha, Khanh ^{[1
]}

Chahar, Mamta ^{[1
]}

Monbaliu, Jean-Christophe M. ^{[1
,2
]}

Todadze, Ekaterina ^{[1
]}

Hansen, Finn K. ^{[1
,3
]}

Oliferenko, Alexander A. ^{[1
]}

Ocampo, Charles E. ^{[1
]}

Leino, David ^{[1
]}

Lillicotch, Aaron ^{[1
]}

Stevens, Christian V. ^{[2
]}

Katritzky, Alan R. ^{[1
,4
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, B-9000 Ghent, Belgium

[3] Univ Dusseldorf, Inst Pharmazeut & Med Chem, D-40225 Dusseldorf, Germany

[4] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期

关键词：

CHEMICAL LIGATION; STABILITY; ACIDS; DIMER;

D O I：

10.1021/jo2023125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2637 / 2648

页数：12

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