Details

Autor(en) / Beteiligte

• 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

Titel

Intramolecular Hydrogen Bonding in N[sup.6]-Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy

Ist Teil von

• International journal of molecular sciences, 2023-06, Vol.24 (11)

Ort / Verlag

MDPI AG

Erscheinungsjahr

2023

Link zum Volltext

Quelle

EZB Free E-Journals

Beschreibungen/Notizen

• Two forms were found in the NMR spectra of N[sup.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, [sup.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[sup.6]-CH proton of the substituent. The [sup.1]H,[sup.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[sup.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.