Conformation and proton configuration of pyrimidine deoxynucleoside oxidation damage products in water
Conformation and proton configuration of pyrimidine deoxynucleoside oxidation damage products in water
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DOI：
10.1021/tx990209u
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发表时间：
2000-06-01
影响因子：
4.1
通讯作者：
Sowers, LC
中科院分区：
文献类型：
--
作者：
La Francois, CJ;Jang, YH;Sowers, LC
新出现的数据有力地表明，DNA碱基的氧化可能导致基因组的不稳定。碱基氧化引起的DNA结构变化可能降低DNA复制的保真度并干扰序列特异性DNA-蛋白质相互作用。研究了一系列嘧啶脱氧核苷氧化损伤产物在水溶液中的结构。所研究的修饰核苷包括5-羟基尿嘧啶、5-羟基胞嘧啶、5-（羟甲基）尿嘧啶、5-（羟甲基）胞嘧啶、5-甲酰基尿嘧啶和5-甲酰基胞嘧啶的脱氧核苷衍生物。根据n -15富集衍生物的紫外、质子和氮核磁共振光谱，确定了碱氧化对电离常数、糖构象和互变异构体构型的影响。潜在的生物学。讨论了碱氧化引起的结构扰动的后果。
Emerging data strongly suggest that the oxidation of DNA bases can contribute to genomic instability. Structural changes to DNA, induced by base oxidation, may reduce the fidelity of DNA replication and interfere with sequence-specific DNA-protein interactions. We have examined the structures of a series of pyrimidine deoxynucleoside oxidation damage products in aqueous solution. The modified nucleosides studied include the deoxynucleoside derivatives of 5-hydroxyuracil, 5-hydroxycytosine, 5-(hydroxymethyl)uracil, 5-(hydroxymethyl)cytosine, 5-formyluracil, and 5-formylcytosine. The influence of base oxidation on ionization constants, sugar conformation, and tautomeric configuration has been determined on the basis of UV, proton, and nitrogen NMR spectra of the N-15-enriched derivatives. The potential biological. consequences of the structural perturbations resulting from base oxidation are discussed.