N-ALKOXYCARBONYL AMINO-ACID N-CARBOXYANHYDRIDES AND N,N-DIALKOXYCARBONYL AMINO-ACID FLUORIDES FROM N,N-DIPROTECTED AMINO-ACIDS

被引：24

作者：

SAVRDA, J ^{[1
]}

WAKSELMAN, M ^{[1
]}

机构：

[1] CNRS,CTR ETUD & RECH CHIM ORGAN APPL,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 11期

关键词：

D O I：

10.1039/c39920000812

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Activation of N,N-bis-Boc or N-Boc N-Z amino acids with SOCl2-DMF leads to N-protected N-carboxy amino acid anhydrides, whereas treatment with cyanuric fluoride at low temperature gives mainly N,N-bis-protected amino acid fluorides, which are efficient acylating agents.

引用

页码：812 / 813

页数：2

共 17 条

[1]

Bergmann M, 1935, J BIOL CHEM, V111, P245

[2] AMINO-ACID FLUORIDES - THEIR PREPARATION AND USE IN PEPTIDE-SYNTHESIS [J].

BERTHO, JN ;

LOFFET, A ;

PINEL, C ;

REUTHER, F ;

SENNYEY, G .

TETRAHEDRON LETTERS, 1991, 32 (10) :1303-1306

[3] EINE METHODE ZUR KATALYSIERTEN HERSTELLUNG VON CARBONSAURE UND SULFOSAURE-CHLORIDEN MIT THIONYLCHLORID [J].

BOSSHARD, HH ;

MORY, R ;

SCHMID, M ;

ZOLLINGER, H .

HELVETICA CHIMICA ACTA, 1959, 42 (05) :1653-1658

[4] TERT-BUTYLOXYCARBONYL AND BENZYLOXYCARBONYL AMINO-ACID FLUORIDES - NEW, STABLE RAPID-ACTING ACYLATING AGENTS FOR PEPTIDE-SYNTHESIS [J].

CARPINO, LA ;

MANSOUR, EME ;

SADATAALAEE, D .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2611-2614

[5] 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

[6] DI-TERT-BUTYL N-ACYLIMIDODICARBONATES AS ISOLABLE ACYLATING AGENTS - MILD CONVERSION OF PRIMARY CARBOXAMIDES TO SUBSTITUTED AMIDES [J].

DAVIDSEN, SK ;

MAY, PD ;

SUMMERS, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5482-5485

[7] A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].

FLYNN, DL ;

ZELLE, RE ;

GRIECO, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426

[8] URETHANE-PROTECTED AMINO-ACID N-CARBOXY ANHYDRIDES AND THEIR USE IN PEPTIDE-SYNTHESIS [J].

FULLER, WD ;

COHEN, MP ;

SHABANKAREH, M ;

BLAIR, RK ;

GOODMAN, M ;

NAIDER, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7414-7416

[9]

FULLER WD, 1991, PEPTIDES 1990, P45

[10]

GUIBEJAMPEL E, 1977, SYNTHESIS-STUTTGART, P772

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