Direct preparation of peptide thioesters using an Fmoc solid-phase method

被引:161
作者
Li, XQ [1 ]
Kawakami, T [1 ]
Aimoto, S [1 ]
机构
[1] Osaka Univ, Inst Prot Res, Osaka 5650871, Japan
关键词
peptides and polypeptides; thioesters; deblocking; solid-phase synthesis;
D O I
10.1016/S0040-4039(98)01868-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aiming at the direct preparation of peptide thioesters by an Fmoc solid-phase method, we searched a new deblocking reagent, which efficiently removed Fmoc groups while keeping the thioester intact. The deblocking reagent, which contains 1-methylpyrrolidine, hexamethyleneimine and HOBt in a one to one mixture of NMP and DMSO, realized the preparation of peptide thioesters by an Fmoc solid-phase method in a yield equivalent to that obtained by a Boc solid-phase method. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8669 / 8672
页数:4
相关论文
共 13 条
[1]  
AHTERTON E, 1978, J CHEM SOC CHEM COMM, P537
[2]   Extending the applicability of native chemical ligation [J].
Canne, LE ;
Bark, SJ ;
Kent, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :5891-5896
[3]  
CHANG CD, 1978, INT J PEPT PROT RES, V11, P246
[4]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[5]   SOLVATION EFFECTS IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].
FIELDS, GB ;
FIELDS, CG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4202-4207
[6]   Total chemical synthesis of enzymatically active human type II secretory phospholipase A(2) [J].
Hackeng, TM ;
Mounier, CM ;
Bon, C ;
Dawson, PE ;
Griffin, JH ;
Kent, SBH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (15) :7845-7850
[7]   POLYPEPTIDE-SYNTHESIS USING THE S-ALKYL THIOESTER OF A PARTIALLY PROTECTED PEPTIDE SEGMENT - SYNTHESIS OF THE DNA-BINDING DOMAIN OF C-MYB PROTEIN (142-193)-NH2 [J].
HOJO, H ;
AIMOTO, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (01) :111-117
[8]   Condensation of Cys(Acm)-containing peptide segments with silver chloride as an activator of peptide thioesters [J].
Kawakami, T ;
Aimoto, S .
CHEMISTRY LETTERS, 1997, (11) :1157-1158
[9]   CHEMICAL SYNTHESIS OF PEPTIDES AND PROTEINS [J].
KENT, SBH .
ANNUAL REVIEW OF BIOCHEMISTRY, 1988, 57 :957-989
[10]  
KING DS, 1990, INT J PEPT PROT RES, V36, P255