SYNTHESIS OF 4-PHOSPHONO-DL-PHENYLALANINE AND OF 4-(PHOSPHONOMETHYL)-DL-PHENYLALANINE, 2 ANALOGS OF O-PHOSPHOTYROSINE

被引:25
作者
BAYLELACOSTE, M
MOULINES, J
COLLIGNON, N
BOUMEKOUEZ, A
DETINGUYMOREAUD, E
NEUZIL, E
机构
[1] INST NATL SCI APPL,IRCOF,COMPOSES ORGANOPHOSPHORES LAB,F-76131 MONT ST AIGNAN,FRANCE
[2] UNIV BORDEAUX 1,CHIM APPL LAB,F-33405 TALENCE,FRANCE
关键词
D O I
10.1016/S0040-4020(01)90076-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
:4-Phosphono-DL-phenylalanine 1 was synthetized from 4-bromo-DL-phenylalanine or from 4-(bromomethyl)-bromobenzene ; 4-(phosphonomethyl)-DL-phenylalanine 14 was prepared from methyl p-toluate. The interest of these phosphonic analogues arises from their possible interference in the metabolism of O-phosphotyrosine. © 1990.
引用
收藏
页码:7793 / 7802
页数:10
相关论文
共 29 条
[1]   SYNTHESIS OF OMEGA-AMINO-OMEGA-CARBOXY-ALKYLPHOSPHONIC ACIDS [J].
ABOUJAOUDE, EE ;
COLLIGNON, N ;
SAVIGNAC, P ;
BENSOAM, J .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 34 (3-4) :93-104
[2]   PROTEIN-KINASE-C ACTIVATION BY DIACYLGLYCEROL 2ND MESSENGERS [J].
BELL, RM .
CELL, 1986, 45 (05) :631-632
[3]   EXPLORATION OF PHENYL-SPACED 2-AMINO-(5-9)-PHOSPHONOALKANOIC ACIDS AS COMPETITIVE N-METHYL-D-ASPARTIC ACID ANTAGONISTS [J].
BIGGE, CF ;
DRUMMOND, JT ;
JOHNSON, G ;
MALONE, T ;
PROBERT, AW ;
MARCOUX, FW ;
COUGHENOUR, LL ;
BRAHCE, LJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1580-1590
[4]   PREPARATION OF AMINOPHENYLPHOSPHONATES, NITROPHENYLPHOSPHONATES, PYRIDYLPHOSPHONATES, AND QUINOLYLPHOSPHONATES UNDER PHOTOSTIMULATION OR METALLIC ASSISTANCE - ACCESS TO CORRESPONDENT AMINOPHOSPHONIC ACIDS [J].
BULOT, JJ ;
ABOUJAOUDE, EE ;
COLLIGNON, N ;
SAVIGNAC, P .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1984, 21 (02) :197-204
[5]  
COHEN S, 1980, J BIOL CHEM, V255, P4834
[6]   REARRANGEMENT AND AMPLIFICATION OF C-ABL SEQUENCES IN THE HUMAN CHRONIC MYELOGENOUS LEUKEMIA-CELL LINE K-562 [J].
COLLINS, SJ ;
GROUDINE, MT .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1983, 80 (15) :4813-4817
[7]  
DAVIS RJ, 1985, J BIOL CHEM, V260, P2543
[8]   ACTIVITY PHOSPHORYLATING TYROSINE IN POLYOMA T-ANTIGEN IMMUNOPRECIPITATES [J].
ECKHART, W ;
HUTCHINSON, MA ;
HUNTER, T .
CELL, 1979, 18 (04) :925-933
[9]   CLONAL ORIGIN OF HUMAN-TUMORS [J].
FIALKOW, PJ .
ANNUAL REVIEW OF MEDICINE, 1979, 30 :135-143
[10]  
FOULKES JG, 1983, CURR TOP MICROBIOL, V107, P163