Mechanism-based inactivation of benzoylformate decarboxylase, a thiamin diphosphate-dependent enzyme

被引：33
|
作者：
Bera, Asim K.
Polovnikova, Lena S.
Roestamadji, Juliatek
Widlanski, Theodore S.
Kenyon, George L.
McLeish, Michael J. [1 ]
Hasson, Miriam S.
机构：
[1] Purdue Univ, Dept Biol Sci, W Lafayette, IN 47907 USA
[2] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[3] Univ Michigan, Coll Pharm, Ann Arbor, MI 48109 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 14期
关键词：
D O I：
10.1021/ja068636z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Benzoylformate decarboxylase (BFD) from Pseudomonas putida is a thiamin diphosphate-dependent enzyme that catalyzes the non-oxidative decarboxylation of benzoylformate. Here we report the discovery of a mechanism-based inhibitor of BFD that is unusual in that it covalently modifies the enzyme via active site phosphorylation. Incubation of BFD with benzoylphosphonate results in time- and concentration-dependent inactivation of the enzyme. X-ray crystallography reveals that the inactivation is due to the phosphorylation of an active site serine residue.
引用
收藏
页码：4120 / +
页数：3
相关论文
共 50 条
  • [21] Spectroscopic detection of transient thiamin diphosphate-bound intermediates on benzoylformate decarboxylase
    Sergienko, EA
    Wang, J
    Polovnikova, L
    Hasson, MS
    McLeish, MJ
    Kenyon, GL
    Jordan, F
    BIOCHEMISTRY, 2000, 39 (45) : 13862 - 13869
  • [22] Molecular mechanism of allosteric substrate activation in a thiamine diphosphate-dependent decarboxylase
    Versees, Wim
    Spaepen, Stijn
    Wood, Martin D. H.
    Leeper, Finian J.
    Vanderleyden, Jos
    Steyaert, Jan
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (48) : 35269 - 35278
  • [23] Thiamin diphosphate in biological chemistry: exploitation of diverse thiamin diphosphate-dependent enzymes for asymmetric chemoenzymatic synthesis
    Mueller, Michael
    Gocke, Doerte
    Pohl, Martina
    FEBS JOURNAL, 2009, 276 (11) : 2894 - 2904
  • [24] Mechanism-based inactivation of dopa decarboxylase by serotonin
    Bertoldi, M
    Moore, PS
    Maras, B
    Dominici, P
    Voltattorni, CB
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (39) : 23954 - 23959
  • [25] Thiamin metabolism and thiamin diphosphate-dependent enzymes in the yeast Saccharomyces cerevisiae:: genetic regulation
    Hohmann, S
    Meacock, PA
    BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1998, 1385 (02): : 201 - 219
  • [26] Intermediates and transition states in thiamin diphosphate-dependent decarboxylases.: A kinetic and NMR study on wild-type indolepyruvate decarboxylase and variants using indolepyruvate, benzoylformate, and pyruvate as substrates
    Schütz, A
    Golbik, R
    König, S
    Hübner, G
    Tittmann, K
    BIOCHEMISTRY, 2005, 44 (16) : 6164 - 6179
  • [27] Use of thiamin diphosphate-dependent decarboxylases in chiral synthesis of carboligase products
    Baykal, AT
    Chakraborty, S
    Nemeria, N
    Jordan, F
    FASEB JOURNAL, 2006, 20 (04): : A40 - A40
  • [28] DIFFERENTIAL REACTIVITY IN THE PROCESSING OF [PARA-(HALOMETHYL)BENZOYL]FORMATES BY BENZOYLFORMATE DECARBOXYLASE, A THIAMIN PYROPHOSPHATE DEPENDENT ENZYME
    REYNOLDS, LJ
    GARCIA, GA
    KOZARICH, JW
    KENYON, GL
    BIOCHEMISTRY, 1988, 27 (15) : 5530 - 5538
  • [29] Multiple modes of active center communication in thiamin diphosphate-dependent enzymes
    Jordan, F
    Nemeria, NS
    Sergienko, E
    ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (09) : 755 - 763
  • [30] C2-α-lactylthiamin diphosphate is an intermediate on the pathway of thiamin diphosphate-dependent pyruvate decarboxylation
    Zhang, S
    Liu, M
    Yan, Y
    Zhang, Z
    Jordan, F
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (52) : 54312 - 54318
12345