Synthetic strategies for polypeptides and proteins by chemical ligation

被引:9
作者
Chen, Ming [1 ]
Heimer, Pascal [1 ]
Imhof, Diana [1 ]
机构
[1] Univ Bonn, Inst Pharm, Pharmaceut Chem 1, D-53119 Bonn, Germany
关键词
Chemical ligation; Native chemical ligation; Thioester; Chemoselective synthesis; Protein synthesis; UNPROTECTED PEPTIDE SEGMENTS; SUGAR-ASSISTED LIGATION; SOLID-PHASE SYNTHESIS; HYDROXYLAMINE KAHA LIGATIONS; PICTET-SPENGLER LIGATION; ORTHOGONAL LIGATION; FUNCTIONAL-CHARACTERIZATION; BIOMIMETIC SYNTHESIS; IONIC LIQUIDS; CYSTEINE;
D O I
10.1007/s00726-015-1982-5
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
This review focuses on chemical ligation methods for the preparation of oligopeptides and proteins. Chemical ligation is a practical and convenient methodology in peptide and protein synthesis. Longer peptides and proteins can be obtained with high yield in aqueous buffer solutions by coupling unprotected peptide segments even without activation by enzymes or further chemical agents. Several methods and protocols were developed in the past. The potential of the most important approaches of the thioester- and imine-ligation techniques is demonstrated by a broad spectrum of applications. In addition, special features and protocols such as the template-directed ligation, ligation with novel additives or solvent media, microwave-assisted ligation, and the achievements obtained with those are also highlighted herein.
引用
收藏
页码:1283 / 1299
页数:17
相关论文
共 180 条
[1]   Hydrazino-Pictet-Spengler Ligation as a Biocompatible Method for the Generation of Stable Protein Conjugates [J].
Agarwal, Paresh ;
Kudirka, Romas ;
Albers, Aaron E. ;
Barfield, Robyn M. ;
de Hart, Gregory W. ;
Drake, Penelope M. ;
Jones, Lesley C. ;
Rabuka, David .
BIOCONJUGATE CHEMISTRY, 2013, 24 (06) :846-851
[2]   A Pictet-Spengler ligation for protein chemical modification [J].
Agarwal, Paresh ;
van der Weijden, Joep ;
Sletten, Ellen M. ;
Rabuka, David ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2013, 110 (01) :46-51
[3]   Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates [J].
Assem, Naila ;
Natarajan, Aditya ;
Yudin, Andrei K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) :10986-10987
[4]   Rapid solid-phase synthesis of a calmodulin-binding peptide using controlled microwave irradiation [J].
Bacsa, Bernadett ;
Kappe, C. Oliver .
NATURE PROTOCOLS, 2007, 2 (09) :2222-2227
[5]   The nature of the bond between peptide and carrier molecule determines the immunogenicity of the construct [J].
Beekman, NJCM ;
Schaaper, WMM ;
Langeveld, JPM ;
Boshuizen, RS ;
Meloen, RH .
JOURNAL OF PEPTIDE RESEARCH, 2001, 58 (03) :237-245
[6]   Design, synthesis and evaluation of antimicrobial activity of N-terminal modified Leucocin A analogues [J].
Bodapati, Krishna Chaitanya ;
Soudy, Rania ;
Etayash, Hashem ;
Stiles, Michael ;
Kaur, Kamaljit .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (13) :3715-3722
[7]   Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids [J].
Bode, JW ;
Fox, RM ;
Baucom, KD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1248-1252
[8]   Ionic liquids as reaction media for oxidative folding and native chemical ligation of cysteine-containing peptides [J].
Boehm, Miriam ;
Tietze, Alesia A. ;
Heimer, Pascal ;
Chen, Ming ;
Imhof, Diana .
JOURNAL OF MOLECULAR LIQUIDS, 2014, 192 :67-70
[9]   Synthesis and Functional Characterization of Tridegin and Its Analogues: Inhibitors and Substrates of Factor XIIIa [J].
Boehm, Miriam ;
Kuehl, Toni ;
Hardes, Kornelia ;
Coch, Richard ;
Arkona, Christoph ;
Schlott, Bernhard ;
Steinmetzer, Torsten ;
Imhof, Diana .
CHEMMEDCHEM, 2012, 7 (02) :326-333
[10]   One-pot chemical synthesis of small ubiquitin-like modifier protein-peptide conjugates using bis(2-sulfanylethyl) amido peptide latent thioester surrogates [J].
Boll, Emmanuelle ;
Drobecq, Herve ;
Ollivier, Nathalie ;
Blanpain, Annick ;
Raibaut, Laurent ;
Desmet, Remi ;
Vicogne, Jerome ;
Melnyk, Oleg .
NATURE PROTOCOLS, 2015, 10 (02) :269-292