Effect of 1-methyladenine on double-helical DNA structures

Methylation at the N1 site of adenine leads to the formation of cytotoxic 1-methyladenine (m1A). Since the N1 site of adenine is involved in the hydrogen bonding of T·A and A·T Watson–Crick base pairs, it is expected that the pairing interactions will be disrupted upon 1-methylation. In this study,...

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Veröffentlicht in:	FEBS letters 2008-05, Vol.582 (11), p.1629-1633
Hauptverfasser:	Yang, Hao, Zhan, Yingqian, Fenn, Dickson, Chi, Lai Man, Lam, Sik Lok
Format:	Artikel
Sprache:	eng
Schlagworte:	1-methyladenine 1-Methylation 2,2-dimethyl-2-silapentane-5-sulfonic acid Adenine Adenine - analogs & derivatives Adenine - chemistry Base Pairing Base Sequence correlation spectroscopy COSY DNA DNA - chemistry DNA Methylation double-quantum-filtered double-stranded DNA DQF dsDNA DSS heteronuclear single quantum coherence spectroscopy Hoogsteen base pair HSQC Hydrogen Bonding m1A m6A N6-methyladenine NMR NOE NOESY nuclear magnetic resonance Nuclear Magnetic Resonance, Biomolecular nuclear Overhauser effect nuclear Overhauser effect spectroscopy Nucleic Acid Conformation one-dimensional PAGE polyacrylamide gel electrophoresis single-stranded DNA ssDNA TOCSY total correlation spectroscopy two-dimensional water suppression by gradient-tailored excitation WATERGATE
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Zusammenfassung:	Methylation at the N1 site of adenine leads to the formation of cytotoxic 1-methyladenine (m1A). Since the N1 site of adenine is involved in the hydrogen bonding of T·A and A·T Watson–Crick base pairs, it is expected that the pairing interactions will be disrupted upon 1-methylation. In this study, high-resolution NMR investigations were performed to determine the effect of m1A on double-helical DNA structures. Interestingly, instead of disrupting hydrogen bonding, we found that 1-methylation altered the T·A Watson–Crick base pair to T( anti)·m1A( syn) Hoogsteen base pair, providing insights into the observed differences in AlkB-repair efficiency between dsDNA and ssDNA.
ISSN:	0014-5793 1873-3468
DOI:	10.1016/j.febslet.2008.04.013