EPIMERIZATION-FREE PEPTIDE FORMATION FROM CARBOXYLIC-ACID ANHYDRIDES AND AZIDO DERIVATIVES

被引:29
作者
BOSCH, I [1 ]
URPI, F [1 ]
VILARRASA, J [1 ]
机构
[1] UNIV BARCELONA,FAC QUIM,DEPT QUIM ORGAN,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1039/c39950000091
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conversion of C-terminal carboxy groups of N-protected alpha-amino acids to the corresponding 3,5-dinitrobenzoyl mixed anhydrides, followed by treatment with alpha-azido eaters and trialkylphosphines, affords good yields of peptides, without appreciable formation of epimers even for reactions involving Phe-Val and Val-Val couplings and/or Nbenroyl alpha-amino acids.
引用
收藏
页码:91 / 92
页数:2
相关论文
共 17 条
[1]   FROM AZIDO ACIDS TO MACROLACTAMS AND MACROLACTONES [J].
BARTRA, M ;
BOU, V ;
GARCIA, J ;
URPI, F ;
VILARRASA, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :270-272
[2]   AN UNEXPECTED REACTION IN THE LACTAMIZATION OF 13-AZIDO-13-DEOXY-(9S)-9-DIHYDROERYTHRONOLIDE-A SECO-ACID DERIVATIVES [J].
BARTRA, M ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON LETTERS, 1992, 33 (25) :3669-3672
[3]   CYCLIZATION OF 9-SUBSTITUTED DECANOIC ACID-DERIVATIVES TO 9-DECANOLIDE AND 9-DECANELACTAM [J].
BARTRA, M ;
VILARRASA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5132-5138
[4]  
Bartra M., 1993, RECENT PROGR CHEM SY, V2, P1
[5]   ALTERNATIVE PROCEDURES FOR THE MACROLACTAMIZATION OF OMEGA-AZIDO ACIDS [J].
BOSCH, I ;
ROMEA, P ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON LETTERS, 1993, 34 (29) :4671-4674
[6]  
BOSCH I, UNPUB J ORG CHHEM
[7]   THE CONVERSION OF CARBOXYLIC-ACIDS TO AMIDES VIA TIN(II) REAGENTS [J].
BURNELLCURTY, C ;
ROSKAMP, EJ .
TETRAHEDRON LETTERS, 1993, 34 (33) :5193-5196
[8]   RACEMIZATION STUDIES DURING SOLID-PHASE PEPTIDE-SYNTHESIS USING AZABENZOTRIAZOLE-BASED COUPLING REAGENTS [J].
CARPINO, LA ;
EL-FAHAM, A ;
ALBERICIO, F .
TETRAHEDRON LETTERS, 1994, 35 (15) :2279-2282
[9]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[10]   PREPARATION OF (R)-2-AZIDOESTERS FROM 2-((PARA-NITROBENZENE)SULFONYL)OXY ESTERS AND THEIR USE AS PROTECTED AMINO-ACID EQUIVALENTS FOR THE SYNTHESIS OF DIPEPTIDES AND TRIPEPTIDES CONTAINING D-AMINO-ACID CONSTITUENTS [J].
HOFFMAN, RV ;
KIM, HO .
TETRAHEDRON, 1992, 48 (15) :3007-3020