TERT-BUTYLOXYCARBONYL AND BENZYLOXYCARBONYL AMINO-ACID FLUORIDES - NEW, STABLE RAPID-ACTING ACYLATING AGENTS FOR PEPTIDE-SYNTHESIS

被引:144
作者
CARPINO, LA
MANSOUR, EME
SADATAALAEE, D
机构
[1] Department of Chemistry, University of Massachusetts, Amherst
关键词
D O I
10.1021/jo00008a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of rapid-acting acylating agents, alpha-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid with cyanuric fluoride.
引用
收藏
页码:2611 / 2614
页数:4
相关论文
共 20 条
[1]  
Bergmann M, 1935, J BIOL CHEM, V111, P245
[2]   A general procedure of the peptide synthesis. [J].
Bergmann, M ;
Zervas, L .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1932, 65 (07) :1192-1201
[3]   The proteolytic fermentation, behaviour of proline pepitide. [J].
Bergmann, M ;
Zervas, L ;
Schleich, H ;
Leinert, F .
HOPPE-SEYLERS ZEITSCHRIFT FUR PHYSIOLOGISCHE CHEMIE, 1932, 212 :72-84
[4]   RAPID CONTINUOUS PEPTIDE-SYNTHESIS VIA FMOC AMINO-ACID CHLORIDE COUPLING AND 4-(AMINOMETHYL)PIPERIDINE DEBLOCKING [J].
BEYERMANN, M ;
BIENERT, M ;
NIEDRICH, H ;
CARPINO, LA ;
SADATAALAEE, D .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :721-728
[6]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID FLUORIDES - CONVENIENT NEW PEPTIDE COUPLING REAGENTS APPLICABLE TO THE FMOC/TERT-BUTYL STRATEGY FOR SOLUTION AND SOLID-PHASE SYNTHESES [J].
CARPINO, LA ;
SADATAALAEE, D ;
CHAO, HG ;
DESELMS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9651-9652
[7]   THE PREPARATION OF N-CARBOXYANHYDRIDES OF ALPHA-AMINO-ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE [J].
DALY, WH ;
POCHE, D .
TETRAHEDRON LETTERS, 1988, 29 (46) :5859-5862
[8]   STUDIES ON THE DIASTEREOISOMERIC AND CONFORMATIONAL ASPECTS OF BENZOYL DIPEPTIDE ESTERS, AS A MEANS OF ASSESSING RACEMIZATION USING NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
DAVIES, JS ;
THOMAS, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1639-1646
[9]   N-TERMINAL SUBSTITUENT AND SIDE-CHAIN INFLUENCES ON THE CHEMICAL-SHIFTS OF PROTONS IN MODEL DIPEPTIDE SYSTEMS [J].
DAVIES, JS ;
HAKEEM, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (08) :1387-1392
[10]   ASSESSMENT OF RACEMIZATION IN N-ALKYLATED AMINO-ACID DERIVATIVES DURING PEPTIDE COUPLING IN A MODEL DIPEPTIDE SYSTEM [J].
DAVIES, JS ;
MOHAMMED, AK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (11) :2982-2990