硫代氮氧化物，RSNHO*：“S-亚硝基血红蛋白”中SNO部分的结构，一种可能的一氧化氮储存库和转运体。
Thionitroxides, RSNHO*: the structure of the SNO moiety in "S-Nitrosohemoglobin", a possible NO reservoir and transporter.
作者信息
Zhao Yi-Lei, Houk K N
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
出版信息
J Am Chem Soc. 2006 Feb 8;128(5):1422-3. doi: 10.1021/ja057097f.
Abstract
Nitric oxide (NO) plays important roles in many biological processes. S-Nitrosothiols have long been believed to have significant roles in NO biochemistry. The modified cysteine residue of hemoglobin was previously identified as a distorted S-nitrosothiol (RSNO) or an S-hydroxyamino radical (RSNOH). Here we show that a thionitroxide (RSNHO, S-aminyloxyl radical) is likely the observed species. Computational studies show that the thionitroxide is the only structure consistent with the electron density in the hemoglobin Cysbeta93-SNO structure previously reported. Although a metastable adduct, the thionitroxide in a hydrogen-bonding environment can form readily and release NO upon exposure to an aqueous environment. The thionitroxides could be responsible for the biological effects attributed to S-nitrosothiols or could serve as precursors to S-nitrosothiols in oxidative conditions.
摘要
一氧化氮（NO）在许多生物过程中发挥着重要作用。长期以来，人们一直认为S-亚硝基硫醇在NO生物化学中具有重要作用。血红蛋白的修饰半胱氨酸残基先前被鉴定为扭曲的S-亚硝基硫醇（RSNO）或S-羟基氨基自由基（RSNOH）。在这里，我们表明硫氧氮自由基（RSNHO，S-氨基氧基自由基）可能是观察到的物种。计算研究表明，硫氧氮自由基是唯一与先前报道的血红蛋白Cysbeta93-SNO结构中的电子密度一致的结构。尽管是一种亚稳加合物，但处于氢键环境中的硫氧氮自由基可以很容易地形成，并在暴露于水环境时释放NO。硫氧氮自由基可能是S-亚硝基硫醇所具有的生物学效应的原因，或者在氧化条件下可以作为S-亚硝基硫醇的前体。
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2
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J Am Chem Soc. 2005 Jun 8;127(22):7964-5. doi: 10.1021/ja042247s.
3
Heme-assisted S-nitrosation of a proximal thiolate in a nitric oxide transport protein.血红素辅助一氧化氮转运蛋白中近端硫醇盐的S-亚硝基化。
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9
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