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在氧饱和水溶液中通过2'-脱氧鸟苷的电离辐射和I型光致敏作用产生的一种新产品的分离与表征:(2S)-2,5'-脱水-1-(2'-脱氧-β-D-赤式-呋喃戊糖基)-5-胍基亚甲基-2-羟基-4-氧代咪唑烷。

Isolation and characterization of a new product produced by ionizing irradiation and type I photosensitization of 2'-deoxyguanosine in oxygen-saturated aqueous solution: (2S)-2,5'-ANHYDRO-1-(2'-deoxy-beta-D-erythro-pentofuranosyl)-5-guanidin ylidene- 2-hydroxy-4-oxoimidazolidine.

作者信息

Buchko G W, Cadet J, Ravanat J L, Labataille P

机构信息

Department of Radiobiology, Cross Cancer Institute, Edmonton, Alberta, Canada.

出版信息

Int J Radiat Biol. 1993 Jun;63(6):669-76. doi: 10.1080/09553009314552061.

DOI:10.1080/09553009314552061
PMID:8100253
Abstract

A major product of the radiation-induced decomposition of 2'-deoxyguanosine in oxygen-saturated aqueous solution has been isolated by reverse phase high performance liquid chromatography and characterized by carbon and proton NMR spectroscopy, fast-atom bombardment mass spectrometry, and chemical analysis as (2S)-2,5'-anhydro-1-(2'-deoxy-beta-D-erythro-pentofuranosyl)-5-guanid inylidene- 2-hydroxy-4-oxoimidazolidine(d < G). This compound is stable in aqueous solution at room temperature but decomposes upon heating (45 degrees C). The lesion is also observed following type I (riboflavin, benzophenone, and acetophenone) photosensitized irradiation of 2'-deoxyguanosine at 350 nm in oxygen-saturated aqueous solution. A similar reaction mechanism, involving a neutral guanine radical intermediate, is proposed to explain the generation of d < G following both types of irradiation.

摘要

通过反相高效液相色谱法分离出了在氧饱和水溶液中2'-脱氧鸟苷辐射诱导分解的一种主要产物,并通过碳和质子核磁共振光谱、快原子轰击质谱以及化学分析将其表征为(2S)-2,5'-脱水-1-(2'-脱氧-β-D-赤藓糖戊呋喃糖基)-5-胍基亚氨基-2-羟基-4-氧代咪唑烷(d<G)。该化合物在室温下的水溶液中稳定,但加热(45摄氏度)时会分解。在氧饱和水溶液中于350nm对2'-脱氧鸟苷进行I型(核黄素、二苯甲酮和苯乙酮)光敏辐射后也观察到了这种损伤。提出了一种类似的反应机制,涉及中性鸟嘌呤自由基中间体,以解释两种辐射后d<G的产生。

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