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Dostęp zamkniętyConformational studies of N-(α-d-glucofuranurono-6,3-lactone)- and N-(methyl β-d-glucopyranuronate)-p-nitroanilines
| cris.lastimport.scopus | 2024-02-12T20:11:26Z |
| dc.abstract.en | N-(α-d-Glucofuranurono-6,3-lactone)-p-nitroaniline and N-(methyl β-d-glucopyranuronate)-p-nitroaniline were obtained as crystalline solids. The single-crystal X-ray diffraction, NMR data and DFT calculations for N-(α-d-glucofuranurono-6,3-lactone)-p-nitroaniline indicate that this N-furanoside adopts a 3T2/3E-like conformation in the crystal lattice, solution and gas phase. Thus, the structure of recorded for N-furanoside 1H NMR spectrum is indicative of the 3T2/3E region of the pseudorotational itinerary for furanose derivatives with α-d-gluco, β-L-ido and α-d-xylo configurations. Moreover, it is concluded that the 1T2/E2/3T2/3E region of the pseudorotational itinerary for furanose derivatives with d-gluco, L-ido and d-xylo configurations should be characterised by the lack of coupling between H2 and H3 protons, irrespective of the anomeric configuration. Such a lack of vicinal coupling is characteristic for some of the trans-oriented furanose ring protons. The single-crystal X-ray diffraction and NMR data for N-(methyl β-d-glucopyranuronate)-p-nitroaniline indicate that this N-glucuronide adopts the 4C1 conformation, both in the crystal lattice and solution. The occurrence of anomeric effects in the presented N-glycosides is discussed. The crystal structure analysis of both N-glycosides gives evidence that the amine group in p-nitroaniline is planar due to the nitrogen sp2 hybridisation. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | Samaszko-Fiertek, Justyna |
| dc.contributor.author | Trzybiński, Damian |
| dc.contributor.author | Sikorski, Artur |
| dc.contributor.author | Walczak, Dominik |
| dc.contributor.author | Liberek, Beata |
| dc.contributor.author | Nowacki, Andrzej |
| dc.contributor.author | Myszka, Henryk |
| dc.date.accessioned | 2024-01-24T20:06:17Z |
| dc.date.available | 2024-01-24T20:06:17Z |
| dc.date.issued | 2017 |
| dc.description.finance | Nie dotyczy |
| dc.description.volume | 446-447 |
| dc.identifier.doi | 10.1016/J.CARRES.2017.05.011 |
| dc.identifier.issn | 0008-6215 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/103550 |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Carbohydrate Research |
| dc.relation.pages | 85-92 |
| dc.rights | ClosedAccess |
| dc.sciencecloud | nosend |
| dc.subject.en | N-Furanoside |
| dc.subject.en | N-Glucuronide |
| dc.subject.en | Ring conformation |
| dc.subject.en | Rotamer |
| dc.subject.en | Delocalization |
| dc.subject.en | Anomeric effect |
| dc.title | Conformational studies of N-(α-d-glucofuranurono-6,3-lactone)- and N-(methyl β-d-glucopyranuronate)-p-nitroanilines |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |