Seela Frank, Xiong Hai, Budow Simone, Eickmeier Henning, Reuter Hans
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Münster, Germany.
Acta Crystallogr C. 2012 Apr;68(Pt 4):o174-8. doi: 10.1107/S0108270112010682. Epub 2012 Mar 20.
The title compound {systematic name: 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[6-(1-benzyl-1H-1,2,3-triazol-4-yl)hex-1-ynyl]pyrimidin-2(1H)-one}, C(24)H(28)N(6)O(4), shows two conformations in the crystalline state, viz. (I-1) and (I-2). The pyrimidine groups and side chains of the two conformers are almost superimposable, while the greatest differences between them are observed for the sugar groups. The N-glycosylic bonds of both conformers adopt similar anti conformations, with χ = -168.02 (12)° for conformer (I-1) and χ = -159.08 (12)° for conformer (I-2). The sugar residue of (I-1) shows an N-type (C3'-endo) conformation, with P = 33.1 (2)° and τ(m) = 29.5 (1)°, while the conformation of the 2'-deoxyribofuranosyl group of (I-2) is S-type (C3'-exo), with P = 204.5 (2)° and τ(m) = 33.8 (1)°. Both conformers participate in hydrogen-bond formation and exhibit identical patterns resulting in three-dimensional networks. Intermolecular hydrogen bonds are formed with neighbouring molecules of different and identical conformations (N-H...N, N-H... O, O-H...N and O-H...O).
标题化合物{系统命名:4-氨基-1-(2-脱氧-β-D-赤藓糖基)-5-[6-(1-苄基-1H-1,2,3-三唑-4-基)己-1-炔基]嘧啶-2(1H)-酮},C(24)H(28)N(6)O(4),在晶体状态下呈现两种构象,即(I-1)和(I-2)。两种构象体的嘧啶基团和侧链几乎重叠,而它们之间最大的差异出现在糖基部分。两种构象体的N-糖苷键均采用相似的反式构象,构象体(I-1)的χ = -168.02 (12)°,构象体(I-2)的χ = -159.08 (12)°。(I-1)的糖残基呈现N型(C3'-内型)构象,P = 33.1 (2)°,τ(m) = 29.5 (1)°,而(I-2)的2'-脱氧核糖呋喃糖基的构象为S型(C3'-外型),P = 204.5 (2)°,τ(m) = 33.8 (1)°。两种构象体均参与氢键形成,并呈现相同的模式,从而形成三维网络。与不同和相同构象的相邻分子形成分子间氢键(N-H...N、N-H...O、O-H...N和O-H...O)。