黄素辅酶的多样作用——自然界最多才多艺的演员。
The diverse roles of flavin coenzymes--nature's most versatile thespians.
作者信息
Mansoorabadi Steven O, Thibodeaux Christopher J, Liu Hung-wen
机构信息
Division of Medicinal Chemistry, College of Pharmacy, University of Texas, Austin, Texas 78712, USA.
出版信息
J Org Chem. 2007 Aug 17;72(17):6329-42. doi: 10.1021/jo0703092. Epub 2007 Jun 20.
Abstract
Flavin coenzymes play a variety of roles in biological systems. This Perspective highlights the chemical versatility of flavins by reviewing research on five flavoenzymes that have been studied in our laboratory. Each of the enzymes discussed in this review [the acyl-CoA dehydrogenases (ACDs), CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase reductase (E3), CDP-4-aceto-3,6-dideoxygalactose synthase (YerE), UDP-galactopyranose mutase (UGM), and type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase (IDI-2)] utilizes flavin in a distinct role. In particular, the catalytic mechanisms of two of these enzymes, UGM and IDI-2, may involve novel flavin chemistry.
摘要
黄素辅酶在生物系统中发挥着多种作用。本综述通过回顾我们实验室对五种黄素酶的研究，突出了黄素的化学多样性。本综述中讨论的每种酶[酰基辅酶A脱氢酶（ACD）、CDP-6-脱氧-L-苏糖-D-甘油-4-己酮糖-3-脱水酶还原酶（E3）、CDP-4-乙酰基-3,6-二脱氧半乳糖合酶（YerE）、UDP-吡喃半乳糖变位酶（UGM）和II型异戊烯基二磷酸：二甲基烯丙基二磷酸异构酶（IDI-2）]都以独特的方式利用黄素。特别是，其中两种酶UGM和IDI-2的催化机制可能涉及新颖的黄素化学。
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本文引用的文献
1
Characterization and mechanistic studies of type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase from Staphylococcus aureus.
Biochemistry. 2007 Jul 17;46(28):8401-13. doi: 10.1021/bi700286a. Epub 2007 Jun 22.
2
Synthesis and analysis of substrate analogues for UDP-galactopyranose mutase: implication for an oxocarbenium ion intermediate in the catalytic mechanism.
Org Lett. 2007 Mar 1;9(5):879-82. doi: 10.1021/ol0631408. Epub 2007 Feb 1.
3
Structure of electron transfer flavoprotein-ubiquinone oxidoreductase and electron transfer to the mitochondrial ubiquinone pool.
Proc Natl Acad Sci U S A. 2006 Oct 31;103(44):16212-7. doi: 10.1073/pnas.0604567103. Epub 2006 Oct 18.
4
Escherichia coli type I isopentenyl diphosphate isomerase: structural and catalytic roles for divalent metals.
J Am Chem Soc. 2006 Sep 6;128(35):11545-50. doi: 10.1021/ja063073c.
5
Inhibition of type 2 isopentenyl diphosphate isomerase from Methanocaldococcus jannaschii by a mechanism-based inhibitor of type 1 isopentenyl diphosphate isomerase.
Bioorg Med Chem. 2006 Oct 1;14(19):6555-9. doi: 10.1016/j.bmc.2006.06.011. Epub 2006 Jun 21.
6
Flavin-dependent halogenases involved in secondary metabolism in bacteria.
Appl Microbiol Biotechnol. 2006 May;70(6):631-41. doi: 10.1007/s00253-005-0232-2. Epub 2006 Mar 17.
7
1,4-Anhydrogalactopyranose is not an intermediate of the mutase catalyzed UDP-galactopyranose/furanose interconversion.
Bioorg Med Chem Lett. 2006 Mar 1;16(5):1123-5. doi: 10.1016/j.bmcl.2005.11.106. Epub 2006 Jan 11.
8
Thermodynamic regulation of human short-chain acyl-CoA dehydrogenase by substrate and product binding.
Biochemistry. 2005 Dec 13;44(49):16043-53. doi: 10.1021/bi051048y.
9
Stereochemical analysis of isopentenyl diphosphate isomerase type II from Staphylococcus aureus using chemically synthesized (S)- and (R)-[2-2H]isopentenyl diphosphates.
Org Lett. 2005 Dec 8;7(25):5677-80. doi: 10.1021/ol0524050.
10
Structure of Thermus thermophilus type 2 isopentenyl diphosphate isomerase inferred from crystallography and molecular dynamics.
Biochem Biophys Res Commun. 2005 Dec 23;338(3):1515-8. doi: 10.1016/j.bbrc.2005.10.114. Epub 2005 Oct 27.
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