Intramolecular Hydrogen Bonding in N6-Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy

Autor: Maria Ya. Berzina, Barbara Z. Eletskaya, Alexei L. Kayushin, Elena V. Dorofeeva, Olga I. Lutonina, Ilya V. Fateev, Olga N. Zhavoronkova, Arthur R. Bashorin, Alexandra O. Arnautova, Olga S. Smirnova, Konstantin V. Antonov, Alexander S. Paramonov, Maxim A. Dubinnyi, Roman S. Esipov, Anatoly I. Miroshnikov, Irina D. Konstantinova
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: International Journal of Molecular Sciences, Vol 24, Iss 11, p 9697 (2023)
Druh dokumentu: article
ISSN: 1422-0067
1661-6596
DOI: 10.3390/ijms24119697
Popis: Two forms were found in the NMR spectra of N6-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, 15N-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 N6–CH proton of the substituent. The 1H,15N-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 N6–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.
Databáze: Directory of Open Access Journals
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