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- W4309406044 abstract "• In depth 1 H, 13 C and 15 N NMR study of antagonists for the A3 AR were performed. • Ligands bearing boron cluster or phenyl modification were compared. • The study revealed syn orientation of the nucleobase. • First X-ray structures of adenosine modified with a boron cluster are disclosed. • Ab initio calculations were performed and are compatible with NMR and X-ray study. Detailed nuclear magnetic resonance (NMR), crystallographic and ab initio studies were performed on derivatives of adenosine and 2’-deoxyadenosine modified with boron clusters or alternatively with a phenyl group at position C8. The conformational study of these compounds showed very good agreement between the results established by these three methods. Substitution with a bulky substituent at C8 of adenosine strongly increased the population of the syn orientation around the glycosidic bond, accompanied by a predominance of the South -type conformation between C2’- endo -C3’- exo and C2’- endo -C1’- exo as well as the presence of the +sc orientation of the exocyclic C(4′)-C(5′) bond. Interestingly, 5’O-H∙∙∙∙N3 scalar coupling across hydrogen bonds was observed in the 1 H- 15 N gHMBC spectrum, indicating intramolecular 5’ O-H∙∙∙N3 hydrogen bond formation as a consequence of the coexistence of the syn orientation, South -type conformation and +sc rotamer. The crystal structures of 5 and 7 are the first reported crystal structures of adenosine-boron cluster derivatives. Substitution with a bulky substituent such as boron cluster (C 2 B 10 H 12 ) on C8 adenosine strongly increases the syn orientation around the glycosidic bond, with more lipophilic areas on the outside of the molecule and more hydrophilic in the center, which may be an important factor in interactions with adenosine receptors." @default.
- W4309406044 created "2022-11-27" @default.
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- W4309406044 date "2023-02-01" @default.
- W4309406044 modified "2023-09-30" @default.
- W4309406044 title "Insights into molecular structure of adenosine-boron cluster conjugates and theirs phenyl isosters as adenosine receptor ligands: Nuclear magnetic resonance, crystallographic and computational studies" @default.
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- W4309406044 doi "https://doi.org/10.1016/j.molstruc.2022.134588" @default.
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