1. 5-Ethynyl-2′-deoxycytidine: a DNA building block with a `clickable' side chain.
- Author
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Seela, Frank, Mei, Hui, Xiong, Hai, Budow, Simone, Eickmeier, Henning, and Reuter, Hans
- Subjects
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ETHYNYL compounds , *DEOXYCYTIDINE , *DNA , *CONFORMATIONAL analysis , *HYDROGEN bonding , *CRYSTAL structure - Abstract
The title compound [systematic name: 4-amino-1-(2-deoxy-β- d- erythro-pentofuranosyl)-5-ethynylpyrimidin-2(1 H)-one], C11H13N3O4, shows two conformations in the crystalline state. The N-glycosylic bonds of both conformers adopt similar conformations, with χ = −149.2 (1)° for conformer (I-1) and −151.4 (1)° for conformer (I-2), both in the anti range. The sugar residue of (I-1) shows a C2′- endo envelope conformation (2 E, S-type), with P = 164.7 (1)° and τm = 36.9 (1)°, while (I-2) shows a major C3′- exo sugar pucker (C3′- exo-C2′- endo, 3 T2, S-type), with P = 189.2 (1)° and τm = 33.3 (1)°. 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. [ABSTRACT FROM AUTHOR]
- Published
- 2012
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