SYNTHESIS OF HUMAN ENDOTHELIN-1 BY REGIOSELECTIVE DISULFIDE FORMATION USING THE SILYL CHLORIDE-SULFOXIDE SYSTEM

被引:15
作者
AKAJI, K [1 ]
NISHIUCHI, H [1 ]
KISO, Y [1 ]
机构
[1] KYOTO PHARMACEUT UNIV, DEPT MED CHEM, YAMASHIMA KU, KYOTO 607, JAPAN
关键词
D O I
10.1016/0040-4039(95)00172-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Human endothelin-1, a 21-amino acid peptide having two intramolecular disulfide bonds, has been synthesized by successive oxidation with iodine and methyltrichlorosilane-diphenylsulfoxide. Acetamidomethyl and tert-butyl groups were employed as the orthogonal thiol protecting groups, The indole ring of the C-terminal Trp residue was protected during the oxidation reaction with the formyl group that was introduced using the formic acid-HCl mixture after the peptide-chain construction.
引用
收藏
页码:1875 / 1878
页数:4
相关论文
共 11 条
[1]   TOTAL SYNTHESIS OF HUMAN INSULIN BY REGIOSELECTIVE DISULFIDE FORMATION USING THE SILYL CHLORIDE SULFOXIDE METHOD [J].
AKAJI, K ;
FUJINO, K ;
TATSUMI, T ;
KISO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11384-11392
[2]   DISULFIDE BOND FORMATION USING THE SILYL CHLORIDE SULFOXIDE SYSTEM FOR THE SYNTHESIS OF A CYSTINE PEPTIDE [J].
AKAJI, K ;
TATSUMI, T ;
YOSHIDA, M ;
KIMURA, T ;
FUJIWARA, Y ;
KISO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4137-4143
[3]   REGIOSELECTIVE DOUBLE DISULFIDE FORMATION USING SILYLCHLORIDE-SULFOXIDE SYSTEM [J].
AKAJI, K ;
FUJINO, K ;
TATSUMI, T ;
KISO, Y .
TETRAHEDRON LETTERS, 1992, 33 (08) :1073-1076
[4]  
ATHERTON E, 1987, PEPTIDES ANAL SYNTHE, V9, P1
[5]   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
[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]   SYNTHESIS OF ALPHA-CONOTOXIN SI, A BICYCLIC TRIDECAPEPTIDE AMIDE WITH 2 DISULFIDE BRIDGES - ILLUSTRATION OF NOVEL PROTECTION SCHEMES AND OXIDATION STRATEGIES [J].
MUNSON, MC ;
BARANY, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10203-10210
[9]   A REVERSIBLE CHEMICAL MODIFICATION OF TRYPTOPHAN RESIDUE [J].
PREVIERO, A ;
COLETTIP.MA ;
CAVADORE, JC .
BIOCHIMICA ET BIOPHYSICA ACTA, 1967, 147 (03) :453-&
[10]   ACETAMIDOMETHYL - NOVEL THIOL PROTECTING GROUP FOR CYSTEINE [J].
VEBER, DF ;
VARGA, SL ;
HIRSCHMA.R ;
MILKOWSK.JD ;
DENKEWAL.RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5456-&