Long-Range Chemical Ligation from N→N Acyl Migrations in Tryptophan Peptides via Cyclic Transition States of 10-to 18-Members

被引：12

作者：

Biswas, Suvendu ^{[1
]}

Kayaleh, Roger ^{[1
]}

Pillai, Girinath G. ^{[1
,2
]}

Seon, Christopher ^{[1
]}

Roberts, Ian ^{[1
]}

Popov, Vadim ^{[1
]}

Alamry, Khalid A. ^{[3
]}

Katritzky, Alan R. ^{[1
,3
]}

机构：

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

[2] Univ Tartu, Dept Chem, EE-50411 Tartu, Estonia

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 26期

关键词：

acyl migration; chemical ligation; peptides; transition states; tryptophan; STAUDINGER LIGATION; NATIVE PEPTIDES; PROTEINS; SCOPE; FORM; CYS;

D O I：

10.1002/chem.201400125

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemical ligations to form native peptides from N -> N acyl migrations in Trp-containing peptides via 10- to 18-membered cyclic transition states are described. In this study, a statistical, predictive model that uses an extensive synthetic and computational approach to rationalize the chemical ligation is reported. N -> N acyl migrations that form longer native peptides without the use of Cys/Ser/Tyr residues or an auxiliary group at the ligation site were achieved. The feasibility of these traceless chemical ligations is supported by the N-C bond distance in N-acyl isopeptides. The intramolecular nature of the chemical ligations is justified by using competitive experiments and theoretical calculations.

引用

页码：8189 / 8198

页数：10