A NOVEL ENZYMATIC DECARBOXYLATION PROCEEDS VIA A THIOL ESTER INTERMEDIATE

被引:7
作者
KAWASAKI, T [1 ]
WATANABE, M [1 ]
OHTA, H [1 ]
机构
[1] KEIO UNIV, FAC SCI & TECHNOL, DEPT CHEM, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN
关键词
D O I
10.1246/bcsj.68.2017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It is proposed that arylmalonate decarboxylase (AMDase)-catalyzed decarboxylation proceeds via a thiol ester intermediate. Kinetics and CD spectra indicated that alpha-bromophenylacetate is a competitive inhibitor. TOF mass data indicated that the inhibitor bound with the enzyme through a thiol ester bond which was formed between a cysteine residue of the enzyme and the carboxyl group of the inhibitor. This result was also supported by reactivation of the enzyme by the addition of 2-mercaptoethanol, which is expected to cleave the enzyme-inhibitor bond via nucleophilic attack on the thiol ester linkage.
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页码:2017 / 2020
页数:4
相关论文
共 16 条
[1]   STUDIES ON THE INHIBITION OF PORCINE PANCREATIC ELASTASE USING ELECTROSPRAY MASS-SPECTROMETRY [J].
APLIN, RT ;
ROBINSON, CV ;
SCHOFIELD, CJ ;
WESTWOOD, NJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1650-1652
[2]  
GEVERS W, 1969, P NATL ACAD SCI USA, V63, P1355
[3]   BINDING OF N-ACETYLGLUCOSAMINE TO LYSOZYME - STUDIES ON CIRCULAR DICHROISM [J].
IKEDA, K ;
HAMAGUCHI, K .
JOURNAL OF BIOCHEMISTRY, 1969, 66 (04) :513-+
[4]   SULFHYDRYL-GROUPS RELATED TO THE CATALYTIC ACTIVITY OF GRAMICIDIN-S-SYNTHETASE-1 OF BACILLUS-BREVIS [J].
KANDA, M ;
HORI, K ;
KUROTSU, T ;
MIURA, S ;
YAMADA, Y ;
SAITO, Y .
JOURNAL OF BIOCHEMISTRY, 1981, 90 (03) :765-771
[5]  
MANAVALAN P, 1983, NATURE, V305, P831, DOI 10.1038/305831a0
[6]   CLONING AND HETEROLOGOUS EXPRESSION OF A NOVEL ARYLMALONATE DECARBOXYLASE GENE FROM ALCALIGENES-BRONCHISEPTICUS KU-1201 [J].
MIYAMOTO, K ;
OHTA, H .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1992, 38 (02) :234-238
[7]   STEREOCHEMISTRY OF ENZYME-CATALYZED DECARBOXYLATION OF ALPHA-METHYL-ALPHA-PHENYLMALONIC ACID [J].
MIYAMOTO, K ;
TSUCHIYA, S ;
OHTA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6256-6257
[8]   PURIFICATION AND PROPERTIES OF A NOVEL ARYLMALONATE DECARBOXYLASE FROM ALCALIGENES-BRONCHISEPTICUS KU-1201 [J].
MIYAMOTO, K ;
OHTA, H .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1992, 210 (02) :475-481
[9]   ENZYME-MEDIATED ASYMMETRIC DECARBOXYLATION OF DISUBSTITUTED MALONIC-ACIDS [J].
MIYAMOTO, K ;
OHTA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4077-4078
[10]   ASYMMETRIC DECARBOXYLATION OF DISUBSTITUTED MALONIC-ACID BY ALCALIGENES-BRONCHISEPTICUS KU 1201 [J].
MIYAMOTO, K ;
OHTA, H .
BIOCATALYSIS, 1991, 5 (01) :49-60