由环氧醛生成1,N2-乙烯基-2'-脱氧鸟苷的机制。
Mechanism of 1,N2-etheno-2'-deoxyguanosine formation from epoxyaldehydes.
作者信息
Petrova Katya V, Jalluri Ravikumar S, Kozekov Ivan D, Rizzo Carmelo J
机构信息
Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee 37235-1822, USA.
出版信息
Chem Res Toxicol. 2007 Nov;20(11):1685-92. doi: 10.1021/tx7001433. Epub 2007 Oct 2.
Abstract
Background levels of etheno adducts have been attributed to the reaction of DNA with 2,3-epoxyaldehydes, a proposed product of lipid peroxidation. We have examined the reaction of (2R,3S)-epoxyhexanal with dGuo to give 7-(1S-hydroxybutyl)-1,N(2)-etheno-dGuo. We observed that the stereochemistry of the side chain scrambled over time. This process provided insight into the mechanism for the formation of 1,N(2)-etheno-dGuo from 4,5-epoxy-2-decenal [Lee, S. H., et al.(2002) Chem. Res. Toxicol. 15, 300-304]. The mechanistic proposal predicts that 2-octenal is a by-product of the reaction. The reaction of 4,5-epoxy-2-decenal was reinvestigated, and the 2-octenal adduct of dGuo was identified as a product of this reaction in support of the mechanistic proposal. Also observed are products that appear to be derived from 2,3-epoxyoctanal, which can be formed through Schiff base formation of 4,5-epoxy-2-decenal with the dGuo followed by hydration of the double bond and retro-aldol reaction.
摘要
乙烯基加合物的背景水平被认为是DNA与2,3-环氧醛反应的结果，2,3-环氧醛是脂质过氧化的一种推测产物。我们研究了(2R,3S)-环氧己醛与dGuo反应生成7-(1S-羟基丁基)-1,N(2)-乙烯基-dGuo的反应。我们观察到侧链的立体化学随时间发生了重排。这一过程为从4,5-环氧-2-癸烯醛形成1,N(2)-乙烯基-dGuo的机制提供了见解[Lee, S. H.等人(2002年)《化学研究毒理学》15, 300 - 304]。该机制推测2-辛烯醛是该反应的副产物。对4,5-环氧-2-癸烯醛的反应进行了重新研究，dGuo的2-辛烯醛加合物被鉴定为该反应的产物，支持了该机制推测。还观察到了似乎源自2,3-环氧辛醛的产物，其可通过4,5-环氧-2-癸烯醛与dGuo形成席夫碱，随后双键水合和逆羟醛反应而形成。
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