POLYPEPTIDES .11. TETRAZOLE ANALOGUES OF C-TERMINAL TETRAPEPTIDE AMIDE SEQUENCE OF GASTRINS

被引:49
作者
MORLEY, JS
机构
[1] Imperial Chemical Industries Limited, Pharmaceuticals Division, Macclesfield, Cheshire, Alderley Park
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 05期
关键词
D O I
10.1039/j39690000809
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis is described of two analogues of N-benzyloxycarbonyl-L- tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide (a physiologically active derivative of the C-terminal tetrapeptide amide sequence of the gastrins) wherein the aspartyl β-carboxy-group or the terminal carboxamide group of the tetrapeptide amide are replaced by a tetrazol-5-yl residue. The optically active amino-acid analogues (carboxy replaced by tetrazol5-yl) required in these syntheses were prepared without special difficulties, and they could be utilised in peptide synthesis without protection of the tetrazole unit.
引用
收藏
页码:809 / &
相关论文
共 15 条
[1]  
BENTLEY PH, 1964, J CHEM SOC, P6130
[2]   POLYPEPTIDES .3. SYNTHESIS OF C-TERMINAL TETRAPEPTIDE SEQUENCE OF GASTRIN ITS OPTICAL ISOMERS AND ACYLATED DERIVATIVES [J].
DAVEY, JM ;
LAIRD, AH ;
MORLEY, JS .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (05) :555-&
[3]   POLYPEPTIDES .X. VARIATIONS OF TRYPTOPHYL POSITION IN C-TERMINAL TETRAPEPTIDE AMIDE SEQUENCE OF GASTRINS [J].
GREGORY, H ;
MORLEY, JS .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (08) :910-&
[4]   POLYPEPTIDES .6. VARIATIONS OF TERMINAL AMIDE POSITION IN C-TERMINAL TETRAPEPTIDE AMIDE SEQUENCE OF GASTRINS [J].
GREGORY, H ;
LAIRD, AH ;
MORLEY, JS ;
SMITH, JM .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (05) :522-&
[5]   STUDIES ON POLYPEPTIDES .25. ADRENOCORTICOTROPIC POTENCY OF AN EICOSAPEPTIDE AMIDE CORRESPONDING TO N-TERMINAL PORTION OF ACTH MOLECULE - CONTRIBUTION TO RELATION BETWEEN PEPTIDE CHAIN-LENGTH AND BIOLOGICAL ACTIVITY [J].
HOFMANN, K ;
YAJIMA, H ;
YANAIHARA, C ;
HUMES, JL ;
LIU, TY ;
YANAIHARA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (23) :4481-&
[6]  
LIBEREK B, 1963, B ACAD POL SCI-CHIM, V11, P677
[7]  
LIBEREK B, 1965, ROCZNIKI CHEM, V39, P369
[8]   TETRAZOLE ANALOGS OF AMINO ACIDS [J].
MCMANUS, JM ;
HERBST, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (11) :1643-1649
[9]  
MORLEY JS, 1968, FED PROC, V27, P1314
[10]   STRUCTURE - FUNCTION RELATIONSHIPS IN GASTRIN-LIKE PEPTIDES [J].
MORLEY, JS .
PROCEEDINGS OF THE ROYAL SOCIETY SERIES B-BIOLOGICAL SCIENCES, 1968, 170 (1018) :97-+