THE ROLE OF DEHYDROALANINE IN CATALYSIS BY HISTIDINE AMMONIA-LYASE

被引:51
作者
LANGER, M [1 ]
PAULING, A [1 ]
RETEY, J [1 ]
机构
[1] UNIV KARLSRUHE,INST ORGAN CHEM,D-76128 KARLSRUHE,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 13-14期
关键词
DEHYDROALANINE; ENZYME CATALYSIS; HISTIDINE; REACTION MECHANISMS;
D O I
10.1002/anie.199514641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not the α‐amino group but the 5‐position of the imidazole ring functions as a nucleophile towards the prosthetic dehydroalanine residue in the deamination of histidine catalyzed by histidine ammonia lyase (HAL) [Eq. (a)]. The results discussed here strongly support this proposal. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1464 / 1465
页数:2
相关论文
共 18 条
[1]   EVIDENCE FOR A CARBANION INTERMEDIATE IN THE ELIMINATION OF AMMONIA FROM L-HISTIDINE CATALYZED BY HISTIDINE AMMONIA-LYASE [J].
FURUTA, T ;
TAKAHASHI, H ;
KASUYA, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3633-3636
[2]  
FURUTA T, 1992, J BIOL CHEM, V267, P12600
[3]  
GIVOT IL, 1969, J BIOL CHEM, V244, P6341
[4]  
Hanson K. R., 1972, ENZYMES, V7, P75
[5]  
HANSON KR, 1972, ENZYMES, V7, P166
[6]   IDENTIFICATION OF SER(143) AS THE SITE OF MODIFICATION IN THE ACTIVE-SITE OF HISTIDINE AMMONIA-LYASE [J].
HERNANDEZ, D ;
STROH, JG ;
PHILLIPS, AT .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1993, 307 (01) :126-132
[7]   4-NITRO-L-HISTIDINE AS A SUBSTRATE FOR HISTIDINE AMMONIA-LYASE - ROLE OF BETA-HYDROGEN ACIDITY IN THE RATE-LIMITING STEP [J].
KLEE, CB ;
KIRK, KL ;
COHEN, LA .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1979, 87 (01) :343-348
[8]  
KLEE CB, 1975, J BIOL CHEM, V250, P5033
[9]   STEREOSPECIFIC IRREVERSIBLE INHIBITION OF HISTIDINE AMMONIA-LYASE BY L-CYSTEINE [J].
KLEE, CB .
BIOCHEMISTRY, 1974, 13 (22) :4501-4507
[10]   MECHANISM OF ACTION OF UROCANASE - SPECIFIC C-13-LABELING OF THE PROSTHETIC NAD+ AND REVISION OF THE STRUCTURE OF ITS ADDUCT WITH IMIDAZOLYLPROPIONATE [J].
KLEPP, J ;
FALLERTMULLER, A ;
GRIMM, K ;
HULL, WE ;
RETEY, J .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1990, 192 (03) :669-676