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Nucleic Acids Research, 1984, Vol. 12, No. 15 6247-6258
© 1984

CHEMISTRY

Proton-Coupled 15N NMR spectra of neutral adn protonated ethenoadenosine and ethenocytidine*

H. Sierzputowska-Gracz1, M. WiewiÓrowski1, L. Kazerski2,+ and W. von Philipsborn3

1Inst. Bioorganic Chemistry, Polish Academy of Sciences 61704 Poznan, Noskowskiego 12 2Inst. Organic Chemistry, Polish Academy of Sciences 00-961 Warszawa, Kasprzaka 44, Poland 3Inst. Organic Chemistry, Univ. Zürich Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Received June 4, 1984. Accepted July 6, 1984.

The 15N chemical shifts and 15N, 1H spin coupling constants were determined in the title compounds using the INEPT pulse sequence and assigned with the aid of selective proton decoupling. The {delta}/15N/ and J/N,H/ values are discussed in terms of involvement of the imidazole ring created by ethenobridging in the electronic structure of the whole molecule. Both spectral parameters indicate that the diligant nitrogen in this ring is the primary site of protonation in these modified nucleosides.

It is concluded that 15N NMR of nucleoside bases can be largely a complementary method to 1H and 13C NMR studies and, in addition, can serve as a direct probe for studies of nitrogen environment in oligomeric fragments of nucleic acids even at moderately strong magnetic fielde due to the higher spectral dispersion compared with 1H and 13C NMR spectra.

*15N NMR Spectroscopy Part XII; Part XI see Ref. 1.

+On leave to the Institute of Organic Chemistry, University of Zürich, 1981–1982


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