SYNTHESIS OF CYSTINE-PEPTIDE BY A NEW DISULFIDE BOND-FORMING REACTION USING THE SILYL CHLORIDE-SULFOXIDE SYSTEM

被引:37
作者
AKAJI, K [1 ]
TATSUMI, T [1 ]
YOSHIDA, M [1 ]
KIMURA, T [1 ]
FUJIWARA, Y [1 ]
KISO, Y [1 ]
机构
[1] KYOTO PHARMACEUT UNIV,DEPT MED CHEM,YAMASHINA KU,KYOTO 607,JAPAN
关键词
D O I
10.1039/c39910000167
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Methyltrichlorosilane or tetrachlorosilane in trifluoroacetic acid, in the presence of diphenylsulphoxide, is found to cleave various S-protecting groups of cysteine to form cystine directly by the reduction-oxidation reaction; this new disulphide bond forming reaction is successfully applied to the syntheses of oxytocin and human brain natriuretic peptide.
引用
收藏
页码:167 / 168
页数:2
相关论文
共 17 条
[1]   A NEW METHOD FOR THE PROTECTION OF THE SULFHYDRYL GROUP DURING PEPTIDE SYNTHESIS [J].
AKABORI, S ;
SAKAKIBARA, S ;
SHIMONISHI, Y ;
NOBUHARA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1964, 37 (03) :433-434
[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]  
ATHERTON E, 1987, PEPTIDES ANAL SYNTHE, V9, P1
[4]   TERTIARY BUTYL GROUP AS A BLOCKING AGENT FOR HYDROXYL, SULFHYDRYL AND AMIDO FUNCTIONS IN PEPTIDE SYNTHESIS [J].
CALLAHAN, FM ;
PAUL, R ;
ANDERSON, GW ;
ZIMMERMAN, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :201-&
[5]   BENZAMIDOMETHYL GROUP AS A THIOL PROTECTING GROUP FOR CYSTEINE, N-METHYLCYSTEINE, AND CORRESPONDING N-TERT-BUTYLOXYCARBONYL DERIVATIVES [J].
CHAKRAVARTY, PK ;
OLSEN, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1270-1271
[6]   ACID STABILITY OF SEVERAL BENZYLIC PROTECTING GROUPS USED IN SOLID-PHASE PEPTIDE SYNTHESIS - REARRANGEMENT OF 0-BENZYLTYROSINE TO 3-BENZYLTYROSINE [J].
ERICKSON, BW ;
MERRIFIELD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3750-3756
[7]   NEW PROCEDURE FOR THE SYNTHESIS OF CYSTINE-PEPTIDES BY OXIDATION OF S-SUBSTITUTED CYSTEINE-PEPTIDES WITH THALLIUM(III) TRIFLUOROACETATE [J].
FUJII, N ;
OTAKA, A ;
FUNAKOSHI, S ;
BESSHO, K ;
YAJIMA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :163-164
[8]  
HISKEY RG, 1981, PEPTIDES, V3, P37
[9]   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
[10]   TRIMETHYLACETAMIDOMETHYL (TACM) GROUP, A NEW PROTECTING GROUP FOR THE THIOL FUNCTION OF CYSTEINE [J].
KISO, Y ;
YOSHIDA, M ;
FUJIWARA, Y ;
KIMURA, T ;
SHIMOKURA, M ;
AKAJI, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (03) :673-675