钼喋呤生物合成：在 MoaA 催化反应中捕获一种不寻常的嘌呤核糖加合物。
Molybdopterin biosynthesis: trapping an unusual purine ribose adduct in the MoaA-catalyzed reaction.
机构信息
Department of Chemistry, Texas A&M University, College Station, Texas 77842, USA.
出版信息
J Am Chem Soc. 2013 Jul 31;135(30):10883-5. doi: 10.1021/ja4041048. Epub 2013 Jul 22.
Abstract
MoaA/MoaC catalyze a remarkable rearrangement reaction in which guanosine-5'-triphosphate (GTP) is converted to cyclic pyranopterin monophosphate (cPMP). In this reaction, the C8 of GTP is inserted between the C2' and the C3' carbons of the GTP ribose. Previous experiments with GTP isotopomers demonstrated that the ribose C3' hydrogen atom is abstracted by the adenosyl radical. This led to a novel mechanistic proposal involving an intermediate with a bond between the C8 of guanine and C3' of the ribose. This paper describes the use of 2',3'-dideoxyGTP to trap this intermediate.
摘要
MoaA/MoaC 催化一种显著的重排反应，其中鸟苷-5'-三磷酸 (GTP) 转化为环吡喃并磷酸单酯 (cPMP)。在该反应中，GTP 的 C8 插入 GTP 核糖的 C2' 和 C3' 碳原子之间。使用 GTP 同位素标记物的先前实验表明，GTP 核糖的 C3' 氢原子被腺嘌呤基自由基夺取。这导致了一个新的机制提议，涉及到一个中间物，其中鸟嘌呤的 C8 与核糖的 C3' 之间存在键。本文描述了使用 2'，3'-二脱氧 GTP 来捕获这个中间物。
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本文引用的文献
1
Identification of a cyclic nucleotide as a cryptic intermediate in molybdenum cofactor biosynthesis.鉴定环核苷酸为钼辅酶生物合成中的隐匿中间产物。
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2
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Biochemistry. 2013 Feb 19;52(7):1134-6. doi: 10.1021/bi3016026. Epub 2013 Feb 4.
3
Purine 5',8-cyclonucleoside lesions: chemistry and biology.嘌呤 5'，8-环核苷损伤：化学与生物学。
Chem Soc Rev. 2011 Mar;40(3):1368-82. doi: 10.1039/c0cs00061b. Epub 2011 Jan 11.
4
ENDOR spectroscopy shows that guanine N1 binds to [4Fe-4S] cluster II of the S-adenosylmethionine-dependent enzyme MoaA: mechanistic implications.电子顺磁共振光谱表明，鸟嘌呤N1与依赖S-腺苷甲硫氨酸的酶MoaA的[4Fe-4S]簇II结合：机理意义。
J Am Chem Soc. 2009 Jul 8;131(26):9184-5. doi: 10.1021/ja903978u.
5
Radical initiation in the class I ribonucleotide reductase: long-range proton-coupled electron transfer?I类核糖核苷酸还原酶中的自由基引发：远程质子耦合电子转移？
Chem Rev. 2003 Jun;103(6):2167-201. doi: 10.1021/cr020421u.
6
Investigation of the early steps of molybdopterin biosynthesis in Escherichia coli through the use of in vivo labeling studies.通过体内标记研究对大肠杆菌中钼蝶呤生物合成早期步骤的研究。
J Biol Chem. 1995 Jan 20;270(3):1082-7. doi: 10.1074/jbc.270.3.1082.
7
The structure of a molybdopterin precursor. Characterization of a stable, oxidized derivative.钼蝶呤前体的结构。一种稳定的氧化衍生物的表征。
J Biol Chem. 1989 Aug 15;264(23):13440-7.
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