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一种在不对称单元中形成两种构象异构体的2'-脱氧胞苷长链连接点击加合物。

A 2'-deoxycytidine long-linker click adduct forming two conformers in the asymmetric unit.

作者信息

Seela Frank, Xiong Hai, Budow Simone, Eickmeier Henning, Reuter Hans

机构信息

Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Münster, Germany.

出版信息

Acta Crystallogr C. 2012 Apr;68(Pt 4):o174-8. doi: 10.1107/S0108270112010682. Epub 2012 Mar 20.

Abstract

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).

摘要

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)。

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