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3′-O-Acetyl-2′-de­oxy­uridine

In the two independent but very similar mol­ecules of the title compound, C(11)H(14)N(2)O(6), both nucleobase fragments are nearly planar (both within 0.01 Å) while the furan­ose rings exhibit (2) E-endo envelope conformations. In the crystal, the two 3′-O-acetyl-2′-de­oxy­uridine mol­ecules form a...

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Detalles Bibliográficos
Autores principales: Doboszewski, Bogdan, Nazarenko, Alexander Y., Nemykin, Victor N.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050423/
https://www.ncbi.nlm.nih.gov/pubmed/21522742
http://dx.doi.org/10.1107/S160053681004938X
Descripción
Sumario:In the two independent but very similar mol­ecules of the title compound, C(11)H(14)N(2)O(6), both nucleobase fragments are nearly planar (both within 0.01 Å) while the furan­ose rings exhibit (2) E-endo envelope conformations. In the crystal, the two 3′-O-acetyl-2′-de­oxy­uridine mol­ecules form a pseudosymmetric dimer of two bases connected via two nearly identical resonance-assisted N—H⋯O hydrogen bonds. The resulting pair is further connected with neighboring pairs via two similar O—H⋯O bonds involving the only hydroxyl group of the 2′-de­oxy­furan­ose fragment and the remaining carbonyl oxygen of the nucleobase. These inter­actions result in the formation of an infinite ‘double band’ along the b axis that can be considered as a self-assembled analogue of a polynucleotide mol­ecule with non-canonical Watson–Crick base pairs. The infinite chains of 3′-O-acetyl-2′-de­oxy­uridine pairs are additionally held together by C—H⋯O inter­actions involving C atoms of the uracyl base and O atoms of carbonyl groups. Only weak C—H⋯O contacts exist between neighboring chains.