Inactivation of serine protease, alpha-chymotrypsin by fluorinated phenylalanine analogues

被引:41
作者
Ohba, T [1 ]
Ikeda, E [1 ]
Takei, H [1 ]
机构
[1] TOKYO INST TECHNOL,INTERDISCIPLINARY GRAD SCH SCI & ENGN,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN
关键词
D O I
10.1016/0960-894X(96)00342-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1875 / 1880
页数:6
相关论文
共 22 条
[1]   ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].
ANGELASTRO, MR ;
MEHDI, S ;
BURKHART, JP ;
PEET, NP ;
BEY, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13
[2]   TIGHT-BINDING INHIBITORS .1. KINETIC-BEHAVIOR [J].
CHA, S .
BIOCHEMICAL PHARMACOLOGY, 1975, 24 (23) :2177-2185
[3]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[4]   THE DETERMINATION OF ENZYME INHIBITOR CONSTANTS [J].
DIXON, M .
BIOCHEMICAL JOURNAL, 1953, 55 (01) :170-171
[5]  
FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
[6]   STRUCTURE AND STEREOCHEMISTRY OF TETRAHEDRAL INHIBITOR COMPLEXES OF PAPAIN BY DIRECT NMR OBSERVATION [J].
GAMCSIK, MP ;
MALTHOUSE, JPG ;
PRIMROSE, WU ;
MACKENZIE, NE ;
BOYD, ASF ;
RUSSELL, RA ;
SCOTT, AI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (20) :6324-6325
[7]   AN IMPROVED ONE-POT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF THE (2S,3R)-3-AMINO-2-HYDROXY ACIDS - KEY INTERMEDIATES FOR BESTATIN AND AMASTATIN [J].
HERRANZ, R ;
CASTROPICHEL, J ;
VINUESA, S ;
GARCIALOPEZ, MT .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2232-2234
[8]   INHIBITION OF SERINE PROTEASES BY PEPTIDYL FLUOROMETHYL KETONES [J].
IMPERIALI, B ;
ABELES, RH .
BIOCHEMISTRY, 1986, 25 (13) :3760-3767
[9]   ALPHA,ALPHA-DIFLUOROARYLACETIC ACIDS - PREPARATION FROM (DIETHYLAMINO)SULFUR TRIFLUORIDE AND ALPHA-OXOARYLACETATES [J].
MIDDLETON, WJ ;
BINGHAM, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2883-2887
[10]   NEW FLUORINATING REAGENTS - DIALKYLAMINOSULFUR FLUORIDES [J].
MIDDLETON, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05) :574-578