PMID: 8973643Dec 1, 1996Paper

Methoxyamine-induced mutagenesis of nucleic acids. A proton NMR study of oligonucleotides containing N4-methoxycytosine paired with adenine or guanine

European Journal of Biochemistry
Z GdaniecG V Fazakerley

Abstract

We report the solution structure of two heptanucleotides each containing a central N4-methoxycytosine, in one case paired with adenine on the opposite strand and the other with guanine. For the N4-methoxycytosine adenine pair, only the imino form of the N4-methoxycytosine residue is observed and base pairing is in Watson-Crick geometry. However, rotation of the methoxy group about the N-OCH3 bond is not constrained to a particular orientation although it must be anti to the N3 of N4-methoxycytosine. The slow exchange on a proton NMR time scale between the single strand and double strand forms is attributed to the strong preference of the cis conformation of the OCH3 group in the single strand, which inhibits base pair formation. For the N4-methoxycytosine that is base paired with guanine, we observe an amino form in Watson-Crick geometry in slow exchange with a base paired imino form in wobble geometry. The amino form is predominant at low temperature whereas the imino form predominates above 313 K. We have measured the exchange rate between the two forms at 303 K and observed a value of approximately 1 S-1. The relative ratio of amino and imino forms of N4-methoxycytosine is influenced by both the base that is in front and the...Continue Reading

References

Dec 5, 1990·Journal of Molecular Biology·L Van MeerveltO Kennard
Mar 11, 1987·Nucleic Acids Research·G V FazakerleyW Guschlbauer
Oct 26, 1987·Nucleic Acids Research·N N AnandS A Salisbury
Jan 1, 1968·Journal of the Chemical Society. Perkin Transactions 1·D M BrownP Schell
Dec 16, 1983·Biochemical and Biophysical Research Communications·M RanceK Wüthrich
Mar 5, 1993·Journal of Molecular Biology·G V FazakerleyL C Sowers

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Citations

May 16, 1998·Proceedings of the National Academy of Sciences of the United States of America·F HillD M Brown
Aug 25, 2020·BioEssays : News and Reviews in Molecular, Cellular and Developmental Biology·Denis A SemyonovYury D Nechipurenko
Feb 9, 2006·Chemical Reviews·Mark Lukin, Carlos de Los Santos
Oct 9, 2002·Journal of Pharmaceutical and Biomedical Analysis·E WangA P Cheung
Jun 20, 2000·Chemical Research in Toxicology·C J La FrancoisL C Sowers
Apr 14, 2006·The Journal of Physical Chemistry. a·Leszek LapinskiBorys Kierdaszuk

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