3-胂基丙酮酸的合成及其与磷酸烯醇式丙酮酸变位酶的相互作用。
Synthesis of 3-arsonopyruvate and its interaction with phosphoenolpyruvate mutase.
作者信息
Chawla S, Mutenda E K, Dixon H B, Freeman S, Smith A W
机构信息
Department of Biochemistry, University of Cambridge, U.K.
出版信息
Biochem J. 1995 Jun 15;308 ( Pt 3)(Pt 3):931-5. doi: 10.1042/bj3080931.
Abstract
3-Arsonopyruvate was prepared in four steps from glycine. The arsenic-carbon bond was formed by a Meyer reaction between alkaline arsenite and 2-bromo-3-hydroxy-2-(hydroxymethyl)propionic acid; the 3-arsono-2-hydroxy-2-(hydroxymethyl) propionic acid formed was oxidized with periodate to give 3-arsonopyruvate. This proves to be an alternative substrate for phosphoenolpyruvate mutase, giving pyruvate, which was assayed using lactate dehydrogenase. The K(m) is 20 microM, similar to that observed for the natural substrate phosphonopyruvate (17 microM), whereas the kcat. of 0.01 s-1 was much lower than that for phosphonopyruvate (58 s-1). Arsonopyruvate competitively inhibited the action of the mutase on phosphonopyruvate.
摘要
3-胂丙酮酸由甘氨酸经四个步骤制备而成。通过碱性亚砷酸盐与2-溴-3-羟基-2-(羟甲基)丙酸之间的迈耶反应形成砷-碳键；生成的3-胂基-2-羟基-2-(羟甲基)丙酸用过碘酸盐氧化得到3-胂丙酮酸。事实证明，这是磷酸烯醇丙酮酸变位酶的一种替代底物，可生成丙酮酸，使用乳酸脱氢酶对其进行测定。其米氏常数（K(m)）为20微摩尔，与天然底物膦丙酮酸（17微摩尔）的观测值相似，而其催化常数（kcat.）为0.01秒⁻¹，远低于膦丙酮酸的（58秒⁻¹）。胂丙酮酸竞争性抑制变位酶对膦丙酮酸的作用。
相似文献
1
Synthesis of 3-arsonopyruvate and its interaction with phosphoenolpyruvate mutase.3-胂基丙酮酸的合成及其与磷酸烯醇式丙酮酸变位酶的相互作用。
Biochem J. 1995 Jun 15;308 ( Pt 3)(Pt 3):931-5. doi: 10.1042/bj3080931.
2
Phosphoenolpyruvate mutase catalysis of phosphoryl transfer in phosphoenolpyruvate: kinetics and mechanism of phosphorus-carbon bond formation.磷酸烯醇丙酮酸中磷酸烯醇丙酮酸变位酶催化的磷酰基转移：磷-碳键形成的动力学和机制
Biochemistry. 1996 Apr 9;35(14):4628-35. doi: 10.1021/bi952944k.
3
Cloning, overexpression and mechanistic studies of carboxyphosphonoenolpyruvate mutase from Streptomyces hygroscopicus.
Eur J Biochem. 1992 Oct 15;209(2):735-43. doi: 10.1111/j.1432-1033.1992.tb17342.x.
4
Isolation and characterization of the carbon-phosphorus bond-forming enzyme phosphoenolpyruvate mutase from the mollusk Mytilus edulis.
J Biol Chem. 1998 Feb 20;273(8):4443-8. doi: 10.1074/jbc.273.8.4443.
5
Interaction of inhibitors with phosphoenolpyruvate mutase: implications for the reaction mechanism and the nature of the active site.
Biochemistry. 1994 May 10;33(18):5641-6. doi: 10.1021/bi00184a037.
6
Structure and kinetics of phosphonopyruvate hydrolase from Variovorax sp. Pal2: new insight into the divergence of catalysis within the PEP mutase/isocitrate lyase superfamily.食酸菌属Pal2中膦烯醇丙酮酸水解酶的结构与动力学：对磷酸烯醇式丙酮酸变位酶/异柠檬酸裂合酶超家族内催化作用差异的新见解
Biochemistry. 2006 Sep 26;45(38):11491-504. doi: 10.1021/bi061208l.
7
Sulfuryl transfer catalyzed by pyruvate kinase.丙酮酸激酶催化的硫酸根转移反应。
Biochemistry. 1989 Feb 21;28(4):1604-11. doi: 10.1021/bi00430a027.
8
(Z)-3-(fluoromethyl)phosphoenolpyruvate: synthesis and enzymatic studies.（Z）-3-（氟甲基）磷酸烯醇丙酮酸：合成与酶学研究
Biochemistry. 1988 Feb 23;27(4):1348-55. doi: 10.1021/bi00404a039.
9
Synthesis and study of phosphoenolthiopyruvate.磷酸烯醇硫代丙酮酸的合成与研究
Biochemistry. 1988 Feb 23;27(4):1342-7. doi: 10.1021/bi00404a038.
10
Properties of phosphoenolpyruvate mutase, the first enzyme in the aminoethylphosphonate biosynthetic pathway in Trypanosoma cruzi.磷酸烯醇丙酮酸变位酶的特性，该酶是克氏锥虫中氨基乙基膦酸生物合成途径中的首个酶。
J Biol Chem. 2003 Jun 20;278(25):22703-8. doi: 10.1074/jbc.M302419200. Epub 2003 Apr 2.
引用本文的文献
1
Phylogenomic Analysis of Natural Products Biosynthetic Gene Clusters Allows Discovery of Arseno-Organic Metabolites in Model Streptomycetes.天然产物生物合成基因簇的系统基因组学分析助力在模式链霉菌中发现有机砷代谢产物。
Genome Biol Evol. 2016 Jul 2;8(6):1906-16. doi: 10.1093/gbe/evw125.
2
Arsenic binding to proteins.砷与蛋白质的结合。
Chem Rev. 2013 Oct 9;113(10):7769-92. doi: 10.1021/cr300015c. Epub 2013 Jun 28.
3
Arsenate replacing phosphate: alternative life chemistries and ion promiscuity.砷酸盐取代磷酸盐：替代生命化学和离子混杂性。
Biochemistry. 2011 Feb 22;50(7):1128-34. doi: 10.1021/bi200002a. Epub 2011 Jan 31.
4
Arsenite release on enzymic transformation of arsonomethyl substrate analogues: a potentially lethal synthesis by glycerol-3-phosphate dehydrogenase.砷酸甲酯底物类似物酶促转化过程中砷酸盐的释放：甘油-3-磷酸脱氢酶引发的潜在致命合成反应
Biochem J. 1995 Sep 15;310 ( Pt 3)(Pt 3):983-8. doi: 10.1042/bj3100983.
本文引用的文献
1
Studies on hydroxyamino acids. I. Synthesis of some alpha-alkylated serines.羟基氨基酸的研究。I. 某些α-烷基化丝氨酸的合成。
Arch Biochem Biophys. 1960 Oct;90:254-9. doi: 10.1016/0003-9861(60)90577-4.
2
A rapid spectrophotometric estimation of individual phosphates and phosphonates: its application to chromatography of sugar phosphates and their phosphonate analogues.单个磷酸盐和膦酸盐的快速分光光度法测定：其在糖磷酸盐及其膦酸盐类似物色谱分析中的应用。
Anal Biochem. 1993 Apr;210(1):195-8. doi: 10.1006/abio.1993.1172.
3
Synthesis of 3-arsonoalanine and its action on aspartate aminotransferase and aspartate ammonia-lyase. Comparison with arsenical analogues of malate and fumarate.
Eur J Biochem. 1993 Jul 1;215(1):161-6. doi: 10.1111/j.1432-1033.1993.tb18018.x.
4
Interaction of inhibitors with phosphoenolpyruvate mutase: implications for the reaction mechanism and the nature of the active site.
Biochemistry. 1994 May 10;33(18):5641-6. doi: 10.1021/bi00184a037.
5
Arsenic mononucleotides. Separation by high-performance liquid chromatography and identification with myokinase and adenylate deaminase.砷单核苷酸。通过高效液相色谱法分离并用肌激酶和腺苷酸脱氨酶进行鉴定。
Biochemistry. 1984 Feb 28;23(5):955-60. doi: 10.1021/bi00300a024.
6
The arsonomethyl analogue of adenosine 5'-phosphate. An uncoupler of adenylate kinase.5'-磷酸腺苷的甲酰基类似物。一种腺苷酸激酶解偶联剂。
Biochem J. 1984 Aug 1;221(3):829-36. doi: 10.1042/bj2210829.
7
The mechanism of pyrophosphorolysis of RNA by RNA polymerase. Endowment of RNA polymerase with artificial exonuclease activity.RNA聚合酶对RNA进行焦磷酸解的机制。赋予RNA聚合酶人工核酸外切酶活性。
Biochem J. 1984 Dec 1;224(2):645-50. doi: 10.1042/bj2240645.
8
The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus.蜡样芽孢杆菌将2-氨基乙基膦酸降解过程中2-膦酰基乙醛作为中间产物的鉴定。
Biochim Biophys Acta. 1968 Oct 15;165(3):438-47. doi: 10.1016/0304-4165(68)90223-7.
9
Phosphonate biosynthesis: isolation of the enzyme responsible for the formation of a carbon-phosphorus bond.
Nature. 1988 Sep 29;335(6189):457-8. doi: 10.1038/335457a0.
10
Studies on the biosynthesis of bialaphos (SF-1293). 9. Biochemical mechanism of C-P bond formation in bialaphos: discovery of phosphoenolpyruvate phosphomutase which catalyzes the formation of phosphonopyruvate from phosphoenolpyruvate.双丙氨膦（SF - 1293）的生物合成研究。9. 双丙氨膦中C - P键形成的生化机制：催化磷酸烯醇丙酮酸形成膦酰丙酮酸的磷酸烯醇丙酮酸磷酸变位酶的发现。
J Antibiot (Tokyo). 1989 Mar;42(3):491-4. doi: 10.7164/antibiotics.42.491.
Zotero 插件