PYBOP AND PYBROP - 2 REAGENTS FOR THE DIFFICULT COUPLING OF THE ALPHA,ALPHA-DIALKYL AMINO-ACID, AIB

被引：208

作者：

FREROT, E ^{[1
]}

COSTE, J ^{[1
]}

PANTALONI, A ^{[1
]}

DUFOUR, MN ^{[1
]}

JOUIN, P ^{[1
]}

机构：

[1] CTR CNRS INSERM PHARMACOL ENDOCRINOL,F-34094 MONTPELLIER 5,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)80922-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The difficult coupling of alpha-aminoisobutyric acid (Aib) was carried out using PyBOP(R) and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1 h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.

引用

页码：259 / 270

页数：12

共 31 条

[1] SYNTHESIS AND CHARACTERIZATION OF THE MAJOR COMPONENT OF ALAMETHICIN [J].

BALASUBRAMANIAN, TM ;

KENDRICK, NCE ;

TAYLOR, M ;

MARSHALL, GR ;

HALL, JE ;

VODYANOY, I ;

REUSSER, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6127-6132

[2] STRUCTURE OF TRICHORZIANINE-A IIIC, AN ANTIFUNGAL PEPTIDE FROM TRICHODERMA-HARZIANUM [J].

BODO, B ;

REBUFFAT, S ;

ELHAJJI, M ;

DAVOUST, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) :6011-6017

[3] UNE NOUVELLE SYNTHESE DE LOXYTOCINE [J].

BOISSONNAS, RA ;

GUTTMANN, S ;

JAQUENOUD, PA ;

WALLER, JP .

HELVETICA CHIMICA ACTA, 1955, 38 (06) :1491-1507

[4]

BRUCKNER H, 1989, 2ND FOR PEPT, V174, P251

[5]

CASTRO B, 1975, TETRAHEDRON LETT, P1219

[6]

CASTRO B, 1973, TETRAHEDRON LETT, P3243

[7]

CASTRO B, 1990, PEPTIDES CHEM STRUCT, P900

[8]

CORDOPATIS P, 1984, PEPTIDES 1984, P349

[9] PYBOP - A NEW PEPTIDE COUPLING REAGENT DEVOID OF TOXIC BY-PRODUCT [J].

COSTE, J ;

LENGUYEN, D ;

CASTRO, B .

TETRAHEDRON LETTERS, 1990, 31 (02) :205-208

[10]

COSTE J, 1990, PEPTIDES CHEM STRUCT, P885

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