EFFECT OF TERTIARY BASES ON O-BENZOTRIAZOLYLURONIUM SALT-INDUCED PEPTIDE SEGMENT COUPLING

被引:149
作者
CARPINO, LA
EL-FAHAM, A
机构
[1] Department of Chemistry, University of Massachusetts, Massachusetts 01003-4510, Box 34510, Amherst
关键词
D O I
10.1021/jo00083a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Collidine activation of O-(7-azabenzotriazolyl)-uronium salts leads to relatively low levels of racemization in the coupling of peptide segments, especially with reagents derived from 1,1-carbonyldipyrrolidine.
引用
收藏
页码:695 / 698
页数:4
相关论文
共 37 条
[1]   A REINVESTIGATION OF MIXED CARBONIC ANHYDRIDE METHOD OF PEPTIDE SYNTHESIS [J].
ANDERSON, GW ;
ZIMMERMAN, JE ;
CALLAHAN, FM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :5012-+
[2]   CRYSTAL-STRUCTURE OF 3-(N-ALPHA-TRITYLMETHIONYL)BENZOTRIAZOLE 1-OXIDE, A SYNTHON IN PEPTIDE-SYNTHESIS [J].
BARLOS, K ;
PAPAIOANNOU, D ;
VOLIOTIS, S ;
PREWO, R ;
BIERI, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :696-697
[3]  
BARLOS K, 1984, INT J PEPT PROT RES, V23, P300
[4]  
BODANSZKY M, 1967, J CHEM SOC CHEM COMM, P591
[5]   A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].
BUNIN, BA ;
ELLMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998
[6]   ((9-FLUORENYLMETHYL)OXY)CARBONYL AMINO-ACID CHLORIDES IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
CHAO, HG ;
BEYERMANN, M ;
BIENERT, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2635-2642
[7]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[8]  
CHEN S, 1992, TETRAHEDRON LETT, P647
[9]   OXYBENZOTRIAZOLE FREE PEPTIDE COUPLING REAGENTS FOR N-METHYLATED AMINO-ACIDS [J].
COSTE, J ;
FREROT, E ;
JOUIN, P ;
CASTRO, B .
TETRAHEDRON LETTERS, 1991, 32 (17) :1967-1970
[10]   HYDROLYSIS OF METHYL ETHYLENE PHOSPHATE - STERIC HINDRANCE IN GENERAL BASE CATALYSIS [J].
COVITZ, F ;
WESTHEIMER, FH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (12) :1773-&