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Intramolecular Hydrogen Bonding in N(6)-Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy

Two forms were found in the NMR spectra of N(6)-substituted 2-chloroadenosines. The proportion of the mini-form was 11–32% of the main form. It was characterized by a separate set of signals in COSY, (15)N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an in...

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Detalles Bibliográficos
Autores principales: Berzina, Maria Ya., Eletskaya, Barbara Z., Kayushin, Alexei L., Dorofeeva, Elena V., Lutonina, Olga I., Fateev, Ilya V., Zhavoronkova, Olga N., Bashorin, Arthur R., Arnautova, Alexandra O., Smirnova, Olga S., Antonov, Konstantin V., Paramonov, Alexander S., Dubinnyi, Maxim A., Esipov, Roman S., Miroshnikov, Anatoly I., Konstantinova, Irina D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10253998/
https://www.ncbi.nlm.nih.gov/pubmed/37298648
http://dx.doi.org/10.3390/ijms24119697
Descripción
Sumario:Two forms were found in the NMR spectra of N(6)-substituted 2-chloroadenosines. The proportion of the mini-form was 11–32% of the main form. It was characterized by a separate set of signals in COSY, (15)N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N(6)–CH proton of the substituent. The (1)H,(15)N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N(6)–CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation.