5-Ethynyl-2 `-deoxycytidine: a DNA building block with a `clickable' side chain
Autor(en): | Seela, Frank Mei, Hui Xiong, Hai Budow, Simone Eickmeier, Henning Reuter, Hans |
Stichwörter: | Chemistry; Chemistry, Multidisciplinary; Crystallography | Erscheinungsdatum: | 2012 | Herausgeber: | WILEY-BLACKWELL | Journal: | ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS | Volumen: | 68 | Ausgabe: | 10 | Startseite: | O395-U190 | Zusammenfassung: | The title compound [systematic name: 4-amino-1-(2-deoxy-beta -D-erythro-pentofuranosyl)-5-ethynylpyrimidin-2(1H)-one], C11H13N3O4, shows two conformations in the crystalline state. The N-glycosylic bonds of both conformers adopt similar conformations, with chi = -149.2 (1)degrees for conformer (I-1) and -151.4 (1)degrees for conformer (I-2), both in the anti range. The sugar residue of (I-1) shows a C2'-endo envelope conformation (E-2, S-type), with P = 164.7 (1)degrees and tau(m) = 36.9 (1)degrees, while (I-2) shows a major C3'-exo sugar pucker (C3'-exo-C2'-endo, T-3(2), S-type), with P = 189.2 (1)degrees and tau(m) = 33.3 (1)degrees. Both conformers participate in the formation of a layered three-dimensional crystal structure with a chain-like arrangement of the conformers. The ethynyl groups do not participate in hydrogen bonding, but are arranged in proximal positions. |
ISSN: | 01082701 | DOI: | 10.1107/S0108270112038267 |
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