S- to N-Acyl transfer in S-acylcysteine isopeptides via 9-, 10-, 12-, and 13-membered cyclic transition states

被引：7

作者：

Bol'shakov, Oleg ^{[1
]}

Kovacs, Judit ^{[1
]}

Chahar, Mamta ^{[1
]}

Khanh Ha ^{[1
]}

Khelashvili, Levan ^{[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

来源：

JOURNAL OF PEPTIDE SCIENCE | 2012年 / 18卷 / 11期

关键词：

S- to N-acyl transfer; peptides; cysteine; N-acylbenzotriazoles; S-acylation; PRIOR THIOL CAPTURE; INTRAMOLECULAR O; N-ACYL TRANSFER; NATIVE CHEMICAL LIGATION; PEPTIDE-SYNTHESIS; LIVING CELLS; PROTEINS; AUXILIARY;

D O I：

10.1002/psc.2438

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：

S-Acyl cysteine peptides containing alpha-, beta- or gamma-amino acid residues undergo long-range S- to N-acyl transfer to give analogs of native tripeptides and tetrapeptides containing additional carbon atoms in the chain. The ease of intramolecular S -> N-acyl transfer relative to intermolecular transacylation is favored increasingly for 9?<?12?<?13?similar to?10-membered cyclic transition states; the observed order is explained on conformational and intermolecular interaction considerations. Copyright (c) 2012 European Peptide Society and John Wiley & Sons, Ltd.

引用

页码：704 / 709

页数：6

共 34 条

[1]

[Anonymous], PCMODEL V 9 2 SER SO

[2] 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

[3] Autoregulation of a bacterial σ factor explored by using segmental isotopic labeling and NMR [J].

Camarero, JA ;

Shekhtman, A ;

Campbell, EA ;

Chlenov, M ;

Gruber, TM ;

Bryant, DA ;

Darst, SA ;

Cowburn, D ;

Muir, TW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (13) :8536-8541

[4] Peptide chemical ligation inside living cells: In vivo generation of a circular protein domain [J].

Camarero, JA ;

Fushman, D ;

Cowburn, D ;

Muir, TW .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (09) :2479-2484

[5] Segmental isotopic labeling using expressed protein ligation [J].

Cowburn, D ;

Muir, TW .

NUCLEAR MAGNETIC RESONANCE OF BIOLOGICAL MACROMOLECULES, PT B, 2001, 339 :41-54

[6] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

[7] Synthesis of native proteins by chemical ligation [J].

Dawson, PE ;

Kent, SBH .

ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960

[8] Convergent synthesis of peptide nucleic acids by native chemical Ligation [J].

Dose, C ;

Seitz, O .

ORGANIC LETTERS, 2005, 7 (20) :4365-4368

[9] As fast and selective as enzymatic ligations: Unpaired nucleobases increase the selectivity of DNA-controlled native chemical PNA ligation [J].

Ficht, S ;

Dose, C ;

Seitz, O .

CHEMBIOCHEM, 2005, 6 (11) :2098-2103

[10] Protein semi-synthesis in living cells [J].

Giriat, I ;

Muir, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (24) :7180-7181

← 1 2 3 4 →