Synthesis of cyclic peptides from unprotected precursors using removable Nα-(1-(4-methoxyphenyl)-2-mercaptoethyl) auxiliary

被引:18
作者
Cardona, VMF [1 ]
Hartley, O [1 ]
Botti, P [1 ]
机构
[1] Univ Geneva, Ctr Med, Dept Med Biochem, CH-1211 Geneva, Switzerland
来源
JOURNAL OF PEPTIDE RESEARCH | 2003年 / 61卷 / 03期
关键词
chemical ligation; peptide cyclization; solid-phase synthesis;
D O I
10.1034/j.1399-3011.2003.00043.x
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A new method to cyclize unprotected peptides is presented. The method involves the use of a 1-phenyl-2-mercaptoethyl derivative on the N-terminal glycine. This template acts as an auxiliary thiol-containing group in order to drive cyclization with a counterpart thioester moiety on the same molecule. Subsequent facile removal of the derivative generates products with only native peptide structure. The successful, high-yield cyclization of the peptide GSPYSSDTTPA is described.
引用
收藏
页码:152 / 157
页数:6
相关论文
共 19 条
[1]   Native chemical ligation using removable Nα-(1-phenyl-2-mercaptoethyl) auxiliaries [J].
Botti, P ;
Carrasco, MR ;
Kent, SBH .
TETRAHEDRON LETTERS, 2001, 42 (10) :1831-1833
[2]   Cyclic peptides from linear unprotected peptide precursors through thiazolidine formation [J].
Botti, P ;
Pallin, TD ;
Tam, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) :10018-10024
[3]  
Camarero JA, 1998, ANGEW CHEM INT EDIT, V37, P347, DOI 10.1002/(SICI)1521-3773(19980216)37:3<347::AID-ANIE347>3.0.CO
[4]  
2-5
[5]   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
[6]   CYCLIC PARATHYROID-HORMONE RELATED PROTEIN ANTAGONISTS - LYSINE-13 TO ASPARTIC-ACID 17 [I TO (I + 4)] SIDE-CHAIN TO SIDE-CHAIN LACTAMIZATION [J].
CHOREV, M ;
ROUBINI, E ;
MCKEE, RL ;
GIBBONS, SW ;
GOLDMAN, ME ;
CAULFIELD, MP ;
ROSENBLATT, M .
BIOCHEMISTRY, 1991, 30 (24) :5968-5974
[7]   IDENTIFICATION OF RANTES, MIP-1-ALPHA, AND MIP-1-BETA AS THE MAJOR HIV-SUPPRESSIVE FACTORS PRODUCED BY CD8(+) T-CELLS [J].
COCCHI, F ;
DEVICO, AL ;
GARZINODEMO, A ;
ARYA, SK ;
GALLO, RC ;
LUSSO, P .
SCIENCE, 1995, 270 (5243) :1811-1815
[8]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[9]   POLYMER-BOUND OXIME ESTERS AS SUPPORTS FOR SOLID-PHASE PEPTIDE-SYNTHESIS - PREPARATION OF PROTECTED PEPTIDE-FRAGMENTS [J].
DEGRADO, WF ;
KAISER, ET .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1295-1300
[10]   Protein synthesis by native chemical ligation: Expanded scope by using straightforward methodology [J].
Hackeng, TM ;
Griffin, JH ;
Dawson, PE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (18) :10068-10073