REGIOSELECTIVE DOUBLE DISULFIDE FORMATION USING SILYLCHLORIDE-SULFOXIDE SYSTEM

被引：29

作者：

AKAJI, K ^{[1
]}

FUJINO, K ^{[1
]}

TATSUMI, T ^{[1
]}

KISO, Y ^{[1
]}

机构：

[1] KYOTO PHARMACEUT UNIV,DEPT MED CHEM,YAMASHINA KU,KYOTO 607,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 08期

关键词：

PEPTIDE; DISULFIDE BOND; SILYLCHLORIDE-SULFOXIDE; CONOTOXIN M1; BETA-HANP;

D O I：

10.1016/S0040-4039(00)91864-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two intermolecular or intramolecular disulfide bonds are formed regioselectively by the combination of silylchloride-sulfoxide method with conventional oxidation method. This stepwise method for double disulfide formation is successfully applied to the syntheses of conotoxin M1 and beta-human atrial natriuretic peptide.

引用

页码：1073 / 1076

页数：4

共 14 条

[1] SYNTHESIS OF CYSTINE-PEPTIDE BY A NEW DISULFIDE BOND-FORMING REACTION USING THE SILYL CHLORIDE-SULFOXIDE SYSTEM [J].

AKAJI, K ;

TATSUMI, T ;

YOSHIDA, M ;

KIMURA, T ;

FUJIWARA, Y ;

KISO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (03) :167-168

[2] TETRAFLUOROBORIC ACID AS A USEFUL DEPROTECTING REAGENT IN FLUOREN-9-YLMETHOXYCARBONYL-BASED SOLID-PHASE PEPTIDE SYNTHESES [J].

AKAJI, K ;

YOSHIDA, M ;

TATSUMI, T ;

KIMURA, T ;

FUJIWARA, Y ;

KISO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (04) :288-290

[3] THE SYNTHESIS OF CYSTINE PEPTIDES BY IODINE OXIDATION OF S-TRITYL-CYSTEINE AND S-ACETAMIDOMETHYL-CYSTEINE PEPTIDES [J].

KAMBER, B ;

HARTMANN, A ;

EISLER, K ;

RINIKER, B ;

RINK, H ;

SIEBER, P ;

RITTEL, W .

HELVETICA CHIMICA ACTA, 1980, 63 (04) :899-915

[4] CYSTINE PEPTIDES FROM (S-ACETAMIDOMETHYLCYTEINE) PEPTIDES BY OXYDATION WITH IODINE - SYNTHESIS OF CYCLO-L-CYSTINE [J].

KAMBER, B .

HELVETICA CHIMICA ACTA, 1971, 54 (03) :927-&

[5] STRUCTURAL IDENTIFICATION OF BETA-HUMAN AND GAMMA-HUMAN ATRIAL NATRIURETIC POLYPEPTIDES [J].

KANGAWA, K ;

FUKUDA, A ;

MATSUO, H .

NATURE, 1985, 313 (6001) :397-400

[6]

KUMAGAYE SI, 1988, INT J PEPT PROT RES, V32, P519

[7] SYNTHESIS AND STRUCTURE ACTIVITY STUDY OF MYXOMA VIRUS GROWTH-FACTOR [J].

LIN, YZ ;

KE, XH ;

TAM, JP .

BIOCHEMISTRY, 1991, 30 (13) :3310-3314

[8]

McCurdy S N, 1989, Pept Res, V2, P147

[9] ISOLATION AND STRUCTURE OF A PEPTIDE TOXIN FROM THE MARINE SNAIL CONUS-MAGUS [J].

MCINTOSH, M ;

CRUZ, LJ ;

HUNKAPILLER, MW ;

GRAY, WR ;

OLIVERA, BM .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1982, 218 (01) :329-334

[10]

NAKAGAWA Y, 1981, PEPTIDE CHEM 1980, P41

← 1 2 →