Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: a new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca.

Analogs of 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-(methylthio)pentane, an acyclic intermediate in the methionine salvage pathway: a new preparation and characterization of activity with E1 enolase/phosphatase from Klebsiella oxytoca.
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1-膦酰氧基-2,2-二羟基-3-氧代-5-(甲硫基)戊烷的类似物,甲硫氨酸补救途径中的无环中间体:来自产酸克雷伯氏菌的 E1 烯醇酶/磷酸酶的新制备和活性表征。

DOI:
10.1016/j.bmc.2004.05.002
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发表时间:
2004
影响因子:
3.5
通讯作者:
Pochapsky,ThomasC
Pochapsky,ThomasC
中科院分区:
医学3区
文献类型:
--
作者:
Zhang,Yalin;Heinsen,MelissaH;Kostic,Milka;Pagani,GinaM;Riera,ThomasV;Perovic,Iva;Hedstrom,Lizbeth;Snider,BarryB;Pochapsky,ThomasC

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The methionine salvage pathway allows the in vivo recovery of the methylthio moiety of methionine upon the formation of methylthioadenosine (MTA) from S-adenosylmethionine (SAM). The Fe(II)-containing form of acireductone dioxygenase (ARD) catalyzes the penultimate step in the pathway in Klebsiella oxytoca, the oxidative cleavage of the acireductone 1,2-dihydroxy-3-oxo-5-(methylthio)pent-1-ene (2) by dioxygen to give formate and 2-oxo-4-(methylthio)butyrate (3). The Ni(II)-bound form (Ni–ARD) catalyzes an off-pathway shunt, forming 3-(methylthio)propionate (4), carbon monoxide, and formate. Acireductone 2 is formed by the action of another enzyme, E1 enolase/phosphatase, on precursor 1-phosphonooxy-2,2-dihydroxy-3-oxo-5-methylthiopentane (1). Simple syntheses of several analogs of 1 are described, and their activity as substrates for E1 enolase/phosphatase characterized. A new bacterial overexpression system and purification procedure for E1, a member of the haloacid dehalogenase (HAD) superfamily, is described, and further characterization of the enzyme presented.