Singer B, Spengler S J, Chavez F, Kuśmierek J T
Carcinogenesis. 1987 May;8(5):745-7. doi: 10.1093/carcin/8.5.745.
N2,3-Ethenoguanine (N2,3-epsilon G) was recently identified in the liver of vinyl chloride-exposed rats. We have now synthesized the nucleoside and the 5'-diphosphate which was copolymerized with CDP. The deoxypolynucleotide complement, synthesized by AMV reverse transcriptase contained, in addition to dG, dC and dT. The total pyrimidine content was approximately equivalent to the N2,3-epsilon G content of the template. Incorporation of dC is neither lethal nor mutagenic, while dT incorporation represents a mutagenic event, occurring with approximately 20% frequency. N2,3-epsilon G X dT base pairs can have two hydrogen bonds with minimal helical distortion, as is also the case for N2,3-epsilon G X C base pairs. N2,3-epsilon G is the only derivative formed in vivo by the human carcinogen, vinyl chloride, that can be shown to have a high probability of causing transitions which could initiate malignant transformation.
N2,3-乙烯基鸟嘌呤（N2,3-εG）最近在接触氯乙烯的大鼠肝脏中被发现。我们现已合成了该核苷及其与CDP共聚的5'-二磷酸。由禽成髓细胞瘤病毒逆转录酶合成的脱氧多核苷酸互补链，除了含有dG、dC和dT外，总嘧啶含量大约与模板的N2,3-εG含量相当。dC的掺入既不具有致死性也不具有致突变性，而dT的掺入则代表一种致突变事件，发生频率约为20%。N2,3-εG与dT碱基对可形成两个氢键，螺旋扭曲最小，N2,3-εG与C碱基对也是如此。N2,3-εG是人类致癌物氯乙烯在体内形成的唯一衍生物，已证明其极有可能引发导致恶性转化的转换。
