Artykuł w czasopiśmie
Brak miniatury
Licencja
ClosedAccessDostęp zamknięty
 

Insights into molecular structure of adenosine-boron cluster conjugates and theirs phenyl isosters as adenosine receptor ligands: Nuclear magnetic resonance, crystallographic and computational studies

Uproszczony widok
cris.lastimport.scopus2024-02-12T20:22:42Z
dc.abstract.enDetailed 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 1H-15N 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.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorBaranowski, Daniel
dc.contributor.authorGdaniec, Zofia
dc.contributor.authorLeśnikowski, Zbigniew J.
dc.contributor.authorBednarska-Szczepaniak, Katarzyna
dc.contributor.authorMieczkowski, Adam
dc.date.accessioned2024-01-25T04:19:43Z
dc.date.available2024-01-25T04:19:43Z
dc.date.issued2023
dc.description.financeNie dotyczy
dc.description.number1
dc.description.volume1274
dc.identifier.doi10.1016/J.MOLSTRUC.2022.134588
dc.identifier.issn0022-2860
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/109363
dc.identifier.weblinkhttps://api.elsevier.com/content/article/PII:S0022286022022335?httpAccept=text/xml
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Molecular Structure
dc.relation.pages134588
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enAdenosine receptor ligands
dc.subject.enBoron clusters
dc.subject.enCrystallography
dc.subject.enNMR
dc.subject.enNucleoside conformation
dc.titleInsights into molecular structure of adenosine-boron cluster conjugates and theirs phenyl isosters as adenosine receptor ligands: Nuclear magnetic resonance, crystallographic and computational studies
dc.typeJournalArticle
dspace.entity.typePublication