학술논문
Intramolecular Hydrogen Bonding in N 6 -Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy.
Document Type
Article
Author
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.
Source
Subject
*HYDROGEN bonding
*INTRAMOLECULAR proton transfer reactions
*NUCLEAR magnetic resonance spectroscopy
*NUCLEOSIDES
*ADENOSINE derivatives
*CHEMICAL shift (Nuclear magnetic resonance)
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Language
ISSN
1661-6596
Abstract
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. [ABSTRACT FROM AUTHOR]