APPLICATION OF DIMETHYLSULPHOXIDE(DMSO)/TRIFLUOROACETIC ACID(TFA) OXIDATION TO THE SYNTHESIS OF CYSTINE-CONTAINING PEPTIDE

被引:81
作者
OTAKA, A [1 ]
KOIDE, T [1 ]
SHIDE, A [1 ]
FUJII, N [1 ]
机构
[1] KYOTO UNIV,FAC PHARMACEUT SCI,SAKYO KU,KYOTO 606,JAPAN
关键词
D O I
10.1016/S0040-4039(00)92050-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
S-protected cysteine derivatives [Cys(Trt), Cys(MBzl), Cys(Dbs), Cys(Bzh)] as well as cysteine were converted to cystine by the action of DMSO/TFA; as examples, two model peptides, oxytocin and an alpha-human calcitonin gene-related peptide (alpha-hCGRP), were prepared by this reaction.
引用
收藏
页码:1223 / 1226
页数:4
相关论文
共 16 条
[11]  
KUMAGAYA S, 1988, INT J PEPT PROT RES, V432, P519
[12]   ISOLATION AND CHARACTERIZATION OF HUMAN CALCITONIN GENE-RELATED PEPTIDE [J].
MORRIS, HR ;
PANICO, M ;
ETIENNE, T ;
TIPPINS, J ;
GIRGIS, SI ;
MACINTYRE, I .
NATURE, 1984, 308 (5961) :746-748
[13]  
NISHIMURA O, 1978, CHEM PHARM BULL, V26, P1576
[14]   PROPERTIES AND SUITABILITY OF 10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-YL GROUP (=5-DIBENZOSUBERYL GROUP) AS A NEW PROTECTING GROUP FOR AMINES, AMINO-ACIDS, ALCOHOLS, THIOLS AND CARBOXYLIC-ACIDS [J].
PLESS, J .
HELVETICA CHIMICA ACTA, 1976, 59 (02) :499-512
[15]   REACTIONS OF THIOLS WITH SULFOXIDES .3. CATALYSIS BY ACIDS AND BASES [J].
WALLACE, TJ ;
MAHON, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) :1502-&
[16]   ON CYSTEINE AND CYSTINE PEPTIDES .3. SYNTHESIS OF A FRAGMENT OF INSULIN CONTAINING INTRACHAIN DISULFIDE BRIDGE [J].
ZERVAS, L ;
PHOTAKI, I ;
COSMATOS, A ;
BOROVAS, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (21) :4922-&