N-METHYL N-CARBOXYANHYDRIDE - AN UNEXPECTED BY-PRODUCT WHEN COUPLING BOC-N-METHYL AMINO-ACIDS

被引：28

作者：

FREROT, E ^{[1
]}

COSTE, J ^{[1
]}

PONCET, J ^{[1
]}

JOUIN, P ^{[1
]}

CASTRO, B ^{[1
]}

机构：

[1] CTR PHARMACOL ENDOCRINOL,CNRS,INSERM,RUE CARDONILLE,F-34094 MONTPELLIER 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 20期

关键词：

COUPLING REAGENT; PYBROP; PYCLOP; N-METHYL AMINO ACID; N-CARBOXYANHYDRIDE;

D O I：

10.1016/S0040-4039(00)78866-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Activation of Boc-amino acids and Boc-N-methyl amino acids leads to the corresponding NCA. This side reaction explains the low yields obtained when coupling N-methyl amino acids. It was not observed with the Z- or Fmoc-protective groups.

引用

页码：2815 / 2816

页数：2

共 13 条

[1] 2-ALKOXY-5(4H)-OXAZOLONES FROM N-ALKOXYCARBONYLAMINO ACIDS AND THEIR IMPLICATION IN CARBODIIMIDE-MEDIATED REACTIONS IN PEPTIDE-SYNTHESIS [J].

BENOITON, NL ;

CHEN, FMF .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02) :384-389

[2]

BENOITON NL, 1990, PEPTIDES STRUCTURE F, P889

[3] DECOMPOSITION OF TERT-BUTYLOXYCARBONYLAMINO ACIDS DURING ACTIVATION [J].

BODANSZKY, M ;

KLAUSNER, YS ;

BODANSZKY, A .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (10) :1507-1508

[4]

CHEN FMF, 1978, SYNTHESIS-STUTTGART, P928

[5] SYNTHESIS OF D-LYSINE8-CYCLOSPORINE-A - FURTHER CHARACTERIZATION OF BOP-CL IN THE 2-7 HEXAPEPTIDE FRAGMENT SYNTHESIS [J].

COLUCCI, WJ ;

TUNG, RD ;

PETRI, JA ;

RICH, DH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2895-2903

[6] 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

[7] 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

[8]

HEIMER EP, 1981, INT J PEPT PROT RES, V18, P237

[9] FURTHER-STUDIES ON THE SYNTHESIS OF SYMMETRICAL ANHYDRIDES AND 2,4-DISUBSTITUTED-5(4H)-OXAZOLONES FROM N-ALKOXYCARBONYLAMINO ACIDS USING SOLUBLE CARBODIIMIDE [J].

PAQUET, A ;

CHEN, FMF ;

BENOITON, NL .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1335-1338

[10]

PATINO N, IN PRESS TETRAHEDRON

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