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相对于尿嘧啶衍生物，α-卤代和α-氰基吡啶鎓的加速水解：一种鸟氨酸脱羧酶催化6-氰基尿苷一磷酸水解的模型

Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: a model for ODCase-catalyzed hydrolysis of 6-cyanoUMP.

作者信息

Huang Sha, Wong Freeman M, Gassner George T, Wu Weiming

机构信息

Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, CA 94132 USA.

出版信息

Tetrahedron Lett. 2011 Aug 3;52(31):3960-3962. doi: 10.1016/j.tetlet.2011.05.108.

DOI:10.1016/j.tetlet.2011.05.108
PMID:21799546
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3143031/
Abstract

α-Halo and α-cyano pyridiniums were found to undergo facile hydrolysis, in contrast to the sluggish reactions of corresponding uracils. The greatly enhanced rates found with pyridinium compounds have indicated a possible source of the rate acceleration seen in the hydrolysis of 6-cyanouridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase.

摘要

与相应尿嘧啶的缓慢反应形成对比的是，人们发现α-卤代吡啶鎓和α-氰基吡啶鎓易于发生水解。吡啶鎓化合物反应速率的大幅提高表明，在乳清苷5'-单磷酸脱羧酶催化的6-氰基尿苷5'-单磷酸水解中观察到的速率加速可能有一个来源。

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本文引用的文献

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Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts.取代基常数与吡啶鎓 N - 甲基化学位移之间具有良好的相关性。
Tetrahedron Lett. 2009 Sep 2;50(35):5018-5020. doi: 10.1016/j.tetlet.2009.06.081.
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Substantial formation of hydrates and hemiacetals from pyridinium ketones.吡啶酮大量形成水合物和半缩醛。
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The stability of aryl carbanions derived from pyridine N-oxide: the role of resonance in stabilizing aryl anions.吡啶 N-氧化物衍生的芳基碳负离子的稳定性：共振在稳定芳基阴离子中的作用。
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Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: the role of solvation.吡啶鎓盐和嘧啶鎓盐α位令人惊讶的低水相酸度：溶剂化作用
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5
Formation and stability of a vinyl carbanion at the active site of orotidine 5'-monophosphate decarboxylase: pKa of the C-6 proton of enzyme-bound UMP.乳清苷5'-单磷酸脱羧酶活性位点处乙烯基碳负离子的形成与稳定性：酶结合型UMP的C-6质子的pKa
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Product deuterium isotope effect for orotidine 5'-monophosphate decarboxylase: evidence for the existence of a short-lived carbanion intermediate.乳清苷5'-单磷酸脱羧酶的产物氘同位素效应：存在短寿命碳负离子中间体的证据。
J Am Chem Soc. 2007 Oct 31;129(43):12946-7. doi: 10.1021/ja076222f. Epub 2007 Oct 5.
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Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications.乳清酸类似物脱羧产生的碳负离子：稳定性及其机理意义
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Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase.尿嘧啶类似物6-碳负离子的稳定性：对乳清苷-5'-单磷酸脱羧酶模型反应的机制影响
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An unprecedented twist to ODCase catalytic activity.鸟氨酸脱羧酶催化活性出现前所未有的转折。
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