碱基配对与诱变：通过质子核磁共振观察寡核苷酸中2-氨基嘌呤与胞嘧啶之间的质子化碱基对。
Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR.
作者信息
Sowers L C, Fazakerley G V, Eritja R, Kaplan B E, Goodman M F
出版信息
Proc Natl Acad Sci U S A. 1986 Aug;83(15):5434-8. doi: 10.1073/pnas.83.15.5434.
Abstract
2-Aminopurine (AP), a potent mutagenic base analogue, most frequently pairs with thymine. In the AP X T base pair, both bases adopt normal tautomeric forms. The mechanism for the mutagenic activity arises from its observed pairing with cytosine, which has been ascribed to an enhanced tendency to adopt the rare imino tautomeric form. NMR studies in H2O on all the exchangeable protons in an oligonucleotide duplex containing an AP X T base pair show Watson-Crick hydrogen bonding. When the thymine is replaced by cytosine in the duplex, we observe an AP X C base pair. Both amino protons of AP are seen excluding the rare tautomeric form. Although several alternative structures are possible, it is shown that the second hydrogen bond is formed by protonation of the AP X C base pair and that this is the dominant species under physiological conditions.
摘要
2-氨基嘌呤（AP）是一种强效诱变碱基类似物，最常与胸腺嘧啶配对。在AP与胸腺嘧啶（T）的碱基对中，两个碱基均采用正常的互变异构形式。其诱变活性的机制源于它与胞嘧啶配对的现象，这被归因于AP更倾向于采用罕见的亚氨基互变异构形式。在含有AP与胸腺嘧啶（T）碱基对的寡核苷酸双链体中，对所有可交换质子进行的H2O中的核磁共振（NMR）研究显示出沃森-克里克氢键。当双链体中的胸腺嘧啶被胞嘧啶取代时，我们观察到一个AP与胞嘧啶（C）的碱基对。AP的两个氨基质子均未呈现出罕见的互变异构形式。尽管可能存在几种替代结构，但研究表明，AP与胞嘧啶（C）碱基对的质子化形成了第二个氢键，并且这是生理条件下的主要形式。
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