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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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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
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author Doboszewski, Bogdan
Nazarenko, Alexander Y.
Nemykin, Victor N.
author_facet Doboszewski, Bogdan
Nazarenko, Alexander Y.
Nemykin, Victor N.
author_sort Doboszewski, Bogdan
collection PubMed
description 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.
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spelling pubmed-30504232011-04-26 3′-O-Acetyl-2′-de­oxy­uridine Doboszewski, Bogdan Nazarenko, Alexander Y. Nemykin, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2010-12-04 /pmc/articles/PMC3050423/ /pubmed/21522742 http://dx.doi.org/10.1107/S160053681004938X Text en © Doboszewski et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Doboszewski, Bogdan
Nazarenko, Alexander Y.
Nemykin, Victor N.
3′-O-Acetyl-2′-de­oxy­uridine
title 3′-O-Acetyl-2′-de­oxy­uridine
title_full 3′-O-Acetyl-2′-de­oxy­uridine
title_fullStr 3′-O-Acetyl-2′-de­oxy­uridine
title_full_unstemmed 3′-O-Acetyl-2′-de­oxy­uridine
title_short 3′-O-Acetyl-2′-de­oxy­uridine
title_sort 3′-o-acetyl-2′-de­oxy­uridine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050423/
https://www.ncbi.nlm.nih.gov/pubmed/21522742
http://dx.doi.org/10.1107/S160053681004938X
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