Study of Chemical Ligation Via 17-, 18- and 19-Membered Cyclic Transition States

被引:20
作者
Panda, Siva S. [1 ]
El-Nachef, Claudia [1 ]
Bajaj, Kiran [1 ]
Al-Youbi, Abdulrahman O. [2 ]
Oliferenko, Alexander [1 ]
Katritzky, Alan R. [1 ,2 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
[2] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia
关键词
acyl migration; ligation; molecular modeling; peptide; GLYCOPEPTIDE LIGATION; STAUDINGER LIGATION; PEPTIDE; SCOPE; DIMER;
D O I
10.1111/cbdd.12053
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Unprotected S-acylated cysteine isopeptides containing alpha-, beta- or gamma-amino acid units have been synthesized, and their conversion to native hexapeptides by S- to the N-terminus ligations involving 17-, 18- and 19-membered cyclic transition states have been demonstrated both experimentally and computationally to be more favorable than intermolecular cross-ligations.
引用
收藏
页码:821 / 827
页数:7
相关论文
共 30 条
[1]   Surfaces for Immobilization of N-Terminal Cysteine Derivatives via Native Chemical Ligation [J].
Anderson, Sally .
LANGMUIR, 2008, 24 (24) :13962-13968
[2]   CHEMICAL LIGATION OF CYSTEINE-CONTAINING PEPTIDES - SYNTHESIS OF A 22-KDA TETHERED DIMER OF HIV-1 PROTEASE [J].
BACA, M ;
MUIR, TW ;
SCHNOLZER, M ;
KENT, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1881-1887
[3]   Sugar-assisted glycopeptide ligation with complex oligosaccharides: Scope and limitations [J].
Bennett, Clay S. ;
Dean, Stephen M. ;
Payne, Richard J. ;
Ficht, Simon ;
Brik, Ashraf ;
Wong, Chi-Huey .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :11945-11952
[4]   Synthesis and evaluation of an N-acylated photoactivatable analogue of glutathione as probe for glutathione-utilizing enzymes [J].
Bernardi, D ;
Battaglia, E ;
Kirsch, G .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) :1601-1604
[5]   Chiral aminoalkyl cation equivalents -: 1 -: One-pot synthesis of orthogonally protected enantiopure S-(aminoalkyl)cysteine derivatives [J].
Bolognese, A ;
Fierro, O ;
Guarino, D ;
Longobardo, L ;
Caputo, R .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :169-173
[6]   Sugar-assisted glycopeptide ligation [J].
Brik, A ;
Yang, YY ;
Ficht, S ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5626-5627
[7]   Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis [J].
Chen, Jin ;
Wan, Qian ;
Yuan, Yu ;
Zhu, Jianglong ;
Danishefsky, Samuel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8521-8524
[8]   Native chemical ligation at phenylalanine [J].
Crich, David ;
Banerjee, Abhisek .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10064-+
[9]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[10]   Second-generation sugar-assisted ligation: A method for the synthesis of cysteine-containing glycopeptides [J].
Ficht, Simon ;
Payne, Richard J. ;
Brik, Ashraf ;
Wong, Chi-Huey .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) :5975-5979