An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation

被引:401
作者
Blanco-Canosa, Juan B.
Dawson, Philip E. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
aminoanilides; native chemical ligation; peptides; solid-phase synthesis; thioester;
D O I
10.1002/anie.200705471
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Intramolecular activation of C-terminal peptides: Mildly activated N-acylurea peptides are readily formed on the solid support following chain assembly, avoiding over-activation of the C-terminus. The utility of these peptides is demonstrated by the native chemical ligation of unprotected peptides (see scheme; R = amino acid side chain). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6851 / 6855
页数:5
相关论文
共 39 条
[1]  
Aimoto S, 1999, BIOPOLYMERS, V51, P247, DOI 10.1002/(SICI)1097-0282(1999)51:4<247::AID-BIP2>3.0.CO
[2]  
2-W
[3]   Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis [J].
Backes, BJ ;
Virgilio, AA ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3055-3056
[4]   An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].
Backes, BJ ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330
[5]   Kinetically controlled ligation for the convergent chemical synthesis of proteins [J].
Bang, Duhee ;
Pentelute, Brad L. ;
Kent, Stephen B. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3985-3988
[6]   Native chemical ligation through in situ O to S acyl shift [J].
Botti, P ;
Villain, M ;
Manganiello, S ;
Gaertner, H .
ORGANIC LETTERS, 2004, 6 (26) :4861-4864
[7]   Synthesis of proteins by native chemical ligation using Fmoc-based chemistry [J].
Camarero, JA ;
Mitchell, AR .
PROTEIN AND PEPTIDE LETTERS, 2005, 12 (08) :723-728
[8]   Fmoc-based synthesis of peptide α-thioesters using an aryl hydrazine support [J].
Camarero, JA ;
Hackel, BJ ;
de Yoreo, JJ ;
Mitchell, AR .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4145-4151
[9]   3-thiopropionic acid as a highly versatile multidetachable thioester resin linker [J].
Camarero, JA ;
Adeva, A ;
Muir, TW .
LETTERS IN PEPTIDE SCIENCE, 2000, 7 (01) :17-21
[10]  
Clippingdale AB, 2000, J PEPT SCI, V6, P225, DOI 10.1002/(SICI)1099-1387(200005)6:5<225::AID-PSC244>3.3.CO