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半胱氨酸 S-结合物β-裂合酶:在天然含硫和硒化合物、外源性化合物和抗癌剂的代谢中的重要作用。

Cysteine S-conjugate β-lyases: important roles in the metabolism of naturally occurring sulfur and selenium-containing compounds, xenobiotics and anticancer agents.

机构信息

Department of Biochemistry and Molecular Biology, New York Medical College, Valhalla, USA.

出版信息

Amino Acids. 2011 Jun;41(1):7-27. doi: 10.1007/s00726-010-0552-0. Epub 2010 Mar 22.

Abstract

Cysteine S-conjugate β-lyases are pyridoxal 5'-phosphate-containing enzymes that catalyze β-elimination reactions with cysteine S-conjugates that possess a good leaving group in the β-position. The end products are aminoacrylate and a sulfur-containing fragment. The aminoacrylate tautomerizes and hydrolyzes to pyruvate and ammonia. The mammalian cysteine S-conjugate β-lyases thus far identified are enzymes involved in amino acid metabolism that catalyze β-lyase reactions as non-physiological side reactions. Most are aminotransferases. In some cases the lyase is inactivated by reaction products. The cysteine S-conjugate β-lyases are of much interest to toxicologists because they play an important key role in the bioactivation (toxication) of halogenated alkenes, some of which are produced on an industrial scale and are environmental contaminants. The cysteine S-conjugate β-lyases have been reviewed in this journal previously (Cooper and Pinto in Amino Acids 30:1-15, 2006). Here, we focus on more recent findings regarding: (1) the identification of enzymes associated with high-M(r) cysteine S-conjugate β-lyases in the cytosolic and mitochondrial fractions of rat liver and kidney; (2) the mechanism of syncatalytic inactivation of rat liver mitochondrial aspartate aminotransferase by the nephrotoxic β-lyase substrate S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (the cysteine S-conjugate of tetrafluoroethylene); (3) toxicant channeling of reactive fragments from the active site of mitochondrial aspartate aminotransferase to susceptible proteins in the mitochondria; (4) the involvement of cysteine S-conjugate β-lyases in the metabolism/bioactivation of drugs and natural products; and (5) the role of cysteine S-conjugate β-lyases in the metabolism of selenocysteine Se-conjugates. This review emphasizes the fact that the cysteine S-conjugate β-lyases are biologically more important than hitherto appreciated.

摘要

半胱氨酸 S-结合物β-裂合酶是含有吡哆醛 5'-磷酸的酶,可催化具有β-位良好离去基团的半胱氨酸 S-结合物的β-消除反应。终产物为氨甲酰基丙烯酸和含硫片段。氨甲酰基丙烯酸互变异构并水解为丙酮酸和氨。迄今为止鉴定的哺乳动物半胱氨酸 S-结合物β-裂合酶是参与氨基酸代谢的酶,它们作为非生理副反应催化β-裂合反应。大多数是氨基转移酶。在某些情况下,反应产物会使裂合酶失活。半胱氨酸 S-结合物β-裂合酶对毒理学家非常感兴趣,因为它们在卤代烯烃的生物活化(中毒)中起着重要的关键作用,其中一些卤代烯烃是在工业规模上生产的,并且是环境污染物。本期刊曾对半胱氨酸 S-结合物β-裂合酶进行过综述(Cooper 和 Pinto 在《氨基酸》30:1-15, 2006 年)。在这里,我们重点介绍最近有关以下方面的发现:(1)鉴定与大鼠肝和肾细胞溶质和线粒体部分的高 M(r)半胱氨酸 S-结合物β-裂合酶相关的酶;(2)肾毒性β-裂合酶底物 S-(1,1,2,2-四氟乙基)-L-半胱氨酸(四氟乙烯的半胱氨酸 S-结合物)对大鼠肝线粒体天冬氨酸氨基转移酶同步催化失活的机制;(3)反应性片段从线粒体天冬氨酸氨基转移酶的活性部位到线粒体中易受影响的蛋白质的毒剂通道;(4)半胱氨酸 S-结合物β-裂合酶在药物和天然产物代谢/生物活化中的作用;(5)半胱氨酸 S-结合物β-裂合酶在硒半胱氨酸 Se-结合物代谢中的作用。本综述强调了这样一个事实,即半胱氨酸 S-结合物β-裂合酶比迄今所认识的更为重要。

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