5-(ALPHA-BROMOACETYL)-2'-DEOXYURIDINE 5'-PHOSPHATE - AFFINITY LABEL FOR THYMIDYLATE SYNTHETASE

被引:27
作者
BROUILLETTE, CB [1 ]
CHANG, CTC [1 ]
MERTES, MP [1 ]
机构
[1] UNIV KANSAS,SCH PHARM,DEPT MED CHEM,LAWRENCE,KS 66045
关键词
D O I
10.1021/jm00198a022
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
5-(α-Bromoacetyl)-2ʹ-deoxyuridine 5ʹ-phosphate (1) is an active-site-directed irreversible inhibitor of thymidylate synthetase from Lactobacillus casei. Analysis of the rate of inactivation of the enzyme in the presence of substrate confirmed the intermediate formation of a reversible enzyme-inhibitor complex. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:1541 / 1544
页数:4
相关论文
共 17 条
[1]   5-IODOACETAMIDOMETHYL-2'-DEOXYURIDINE 5'-PHOSPHATE - SELECTIVE INHIBITOR OF MAMMALIAN THYMIDYLATE SYNTHETASES [J].
BARFKNECHT, RL ;
HUETROSE, RA ;
KAMPF, A ;
MERTES, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (16) :5041-5043
[2]   5(ALPHA-BROMOACETYL)-2'-DEOXYURIDINE 5'-PHOSPHATE - MECHANISM BASED AFFINITY LABEL FOR THYMIDYLATE SYNTHETASE [J].
BROUILLETTE, CB ;
CHANG, CTC ;
MERTES, MP .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1979, 87 (02) :613-618
[3]   CHEMISTRY OF ALLENE OXIDES .5. [J].
CHAN, TH ;
ONG, BS .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2994-3001
[4]  
CHANG CC, UNPUBLISHED
[5]   STRUCTURES OF REVERSIBLE AND IRREVERSIBLE COMPLEXES OF THYMIDYLATE SYNTHETASE AND FLUORINATED PYRIMIDINE NUCLEOTIDES [J].
DANENBER.PV ;
LANGENBA.RJ ;
HEIDELBE.C .
BIOCHEMISTRY, 1974, 13 (05) :926-933
[6]   THYMIDYLATE SYNTHETASE - TARGET ENZYME IN CANCER CHEMOTHERAPY [J].
DANENBERG, PV .
BIOCHIMICA ET BIOPHYSICA ACTA, 1977, 473 (02) :73-92
[7]  
FRIEDKIN M, 1973, ADV ENZYMOL RAMB, V38, P235
[8]   SYNTHESIS OF 5-SUBSTITUTED 2'-DEOXYURIDINES [J].
KAMPF, A ;
PILLAR, CJ ;
WOODFORD, WJ ;
MERTES, MP .
JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (07) :909-915
[9]  
KITZ R, 1962, J BIOL CHEM, V237, P3245
[10]   A NEW AND SELECTIVE METHOD OF OXIDATION [J].
KORNBLUM, N ;
POWERS, JW ;
ANDERSON, GJ ;
JONES, WJ ;
LARSON, HO ;
LEVAND, O ;
WEAVER, WM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (24) :6562-6562