Oligonucleotide Incorporation and Base Pair Stability of 9-Deaza-2′-deoxyguanosine, an Analogue of 8-Oxo-2′-deoxyguanosine
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- 作者：Michelle L. Hamm ; Anna J. Parker ; Tyler W. E. Steele ; Jennifer L. Carman ; Carol A. Parish
- 刊名：Journal of Organic Chemistry
- 出版年：2010
- 出版时间：August 20, 2010
- 年：2010
- 卷：75
- 期：16
- 页码：5661-5669
- 全文大小：890K
- 年卷期：v.75,no.16(August 20, 2010)
- ISSN：1520-6904
文摘
9-Deaza-2′-deoxyguanosine (CdG) is a C-nucleoside and an analogue of the abundant promutagen 8-oxo-2′-deoxyguanosine (OdG). Like 2′-deoxyguanosine (dG), CdG should form a stable base pair with dC, but similar to OdG, CdG contains an N7-hydrogen that should allow it to also form a relatively stable base pair with dA. In order to further investigate the base pairing of CdG, it was incorporated into DNA and paired with either dC or dA. Melting studies revealed CdG:dC base pairs are less stable than dG:dC base pairs, while CdG:dA base pairs are less stable than OdG:dA base pairs. In order to gain a deeper understanding of these results, quantum studies on model structures of nucleoside monomers and base pairs were performed, the results of which indicate that (i) CdG:dC base pairs are likely destabilized relative to dG:dC as a result of structural constraints imposed by the C-nucleotide character of CdG, and (ii) CdG:dA base pairs may be less stable than OdG:dA base pairs, at least in part, because of a third long-range interaction that is possible in OdG:dA but not in CdG:dA.