Ring-closing metathesis in peptides

被引:36
作者
Gleeson, Ellen C. [1 ]
Jackson, W. Roy [1 ]
Robinson, Andrea J. [1 ]
机构
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
基金
澳大利亚研究理事会;
关键词
Peptides; Olefin metathesis; Ring-closing metathesis; Dicarba peptides; Cyclic constraints; BOWMAN-BIRK INHIBITOR; ORGANIZATION INDUCED SYNTHESIS; SELECTIVE OLEFIN METATHESIS; ALPHA-HELICAL PEPTIDES; DICARBA-ANALOGS; CHEMICAL-SYNTHESIS; CROSS-METATHESIS; AMINO-ACIDS; MACROCYCLIC PEPTIDES; RUTHENIUM CATALYSTS;
D O I
10.1016/j.tetlet.2016.08.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review highlights developments in the field of ring-closing metathesis applied to the synthesis of cyclic peptides. Special attention is focussed on the synthesis of dicarba peptides that mimic native cystine containing peptides. Recent advances in the field are discussed, including the stereoselective synthesis of carbon-bridged peptides and RCM in aqueous media. Crown Copyright (C) 2016 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:4325 / 4333
页数:9
相关论文
共 119 条
[1]  
[Anonymous], 2012, Drug Discov Today Technol, V9, pe1, DOI 10.1016/j.ddtec.2011.07.003
[2]   α-selenoconotoxins, a new class of potent α7 neuronal nicotinic receptor antagonists [J].
Armishaw, Christopher J. ;
Daly, Norelle L. ;
Nevin, Simon T. ;
Adams, David J. ;
Craik, David J. ;
Alewood, Paul F. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (20) :14136-14143
[3]   Olefin metathesis catalysts bearing a pH-responsive NHC ligand: a feasible approach to catalyst separation from RCM products [J].
Balof, Shawna L. ;
P'Pool, Steven J. ;
Berger, Nancy J. ;
Valente, Edward J. ;
Shiller, Alan M. ;
Schanz, Hans-Joerg .
DALTON TRANSACTIONS, 2008, (42) :5791-5799
[4]   Solid-phase synthesis and DNA binding studies of dichloroplatinum(II) conjugates of dicarba analogues of octreotide as new anticancer drugs [J].
Barragan, Flavia ;
Moreno, Virtudes ;
Marchan, Vicente .
CHEMICAL COMMUNICATIONS, 2009, (31) :4705-4707
[5]  
Berezowska I, 2006, ACTA BIOCHIM POL, V53, P73
[6]   Dicarba analogues of the cyclic enkephalin peptides H-Tyr-c[D-Cys-Gly-Phe-D(or L)-Cys]NH2 retain high opioid activity [J].
Berezowska, Irena ;
Chung, Nga N. ;
Lemieux, Carole ;
Wilkes, Brian C. ;
Schiller, Peter W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (06) :1414-1417
[7]   Cyclic Opioid Peptide Agonists and Antagonists Obtained Via Ring-Closing Metathesis [J].
Berezowska, Irena ;
Lemieux, Carole ;
Chung, Nga N. ;
Wilkes, Brian C. ;
Schiller, Peter W. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 74 (04) :329-334
[8]   Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins [J].
Bernardes, Goncalo J. L. ;
Chalker, Justin M. ;
Errey, James C. ;
Davis, Benjamin G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5052-+
[9]   THE BOWMAN-BIRK INHIBITOR - TRYPSIN-INHIBITOR AND CHYMOTRYPSIN-INHIBITOR FROM SOYBEANS [J].
BIRK, Y .
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1985, 25 (02) :113-131
[10]   Solid-phase synthesis and biological activity of a thioether analogue of conotoxin G1 [J].
Bondebjerg, J ;
Grunnet, M ;
Jespersen, T ;
Meldal, M .
CHEMBIOCHEM, 2003, 4 (2-3) :186-194