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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...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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. |
format | Text |
id | pubmed-3050423 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT doboszewskibogdan 3oacetyl2deoxyuridine AT nazarenkoalexandery 3oacetyl2deoxyuridine AT nemykinvictorn 3oacetyl2deoxyuridine |