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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 03期

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

页码：167 / 168

页数：2

共 17 条

[1] A NEW METHOD FOR THE PROTECTION OF THE SULFHYDRYL GROUP DURING PEPTIDE SYNTHESIS
AKABORI, S
SAKAKIBARA, S
SHIMONISHI, Y
NOBUHARA, Y
[J]. 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
AKAJI, K
YOSHIDA, M
TATSUMI, T
KIMURA, T
FUJIWARA, Y
KISO, Y
[J]. 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
CALLAHAN, FM
PAUL, R
ANDERSON, GW
ZIMMERMAN, JE
[J]. 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
CHAKRAVARTY, PK
OLSEN, RK
[J]. 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
ERICKSON, BW
MERRIFIELD, RB
[J]. 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
FUJII, N
OTAKA, A
FUNAKOSHI, S
BESSHO, K
YAJIMA, H
[J]. 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
KAMBER, B
HARTMANN, A
EISLER, K
RINIKER, B
RINK, H
SIEBER, P
RITTEL, W
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (04) : 899 - 915
[10] TRIMETHYLACETAMIDOMETHYL (TACM) GROUP, A NEW PROTECTING GROUP FOR THE THIOL FUNCTION OF CYSTEINE
KISO, Y
YOSHIDA, M
FUJIWARA, Y
KIMURA, T
SHIMOKURA, M
AKAJI, K
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (03) : 673 - 675

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