Yang Haozhe, Budow Simone, Eickmeier Henning, Reuter Hans, Seela Frank
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstraße 11, 48149 Münster, Germany.
Acta Crystallogr C. 2013 Aug;69(Pt 8):892-5. doi: 10.1107/S0108270113016922. Epub 2013 Jul 9.
The title compound [systematic name: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-nitro-1H-pyrrolo[2,3-b]pyridine], C₁₂H₁₃N₃O₅, forms an intramolecular hydrogen bond between the pyridine N atom as acceptor and the 5'-hydroxy group of the sugar residue as donor. Consequently, the N-glycosylic bond exhibits a syn conformation, with a χ torsion angle of 61.6 (2)°, and the pentofuranosyl residue adopts a C2'-endo envelope conformation (²E, S-type), with P = 162.1 (1)° and τm = 36.2 (1)°. The orientation of the exocyclic C4'-C5' bond is +sc (gauche, gauche), with a torsion angle γ = 49.1 (2)°. The title nucleoside forms an ordered and stacked three-dimensional network. The pyrrole ring of one layer faces the pyridine ring of an adjacent layer. Additionally, intermolecular O-H∙∙∙O and C-H∙∙∙O hydrogen bonds stabilize the crystal structure.
标题化合物[系统名称：1-(2-脱氧-β-D-赤藓糖基)-4-硝基-1H-吡咯并[2,3-b]吡啶]，C₁₂H₁₃N₃O₅，在作为受体的吡啶N原子与作为供体的糖残基的5'-羟基之间形成分子内氢键。因此，N-糖苷键呈现顺式构象，χ扭转角为61.6(2)°，戊呋喃糖残基采用C2'-内型信封构象(²E，S型)，P = 162.1(1)°，τm = 36.2(1)°。环外C4'-C5'键的取向为+sc( gauche，gauche)，扭转角γ = 49.1(2)°。标题核苷形成有序且堆积的三维网络。一层的吡咯环面向相邻层的吡啶环。此外，分子间O-H∙∙∙O和C-H∙∙∙O氢键稳定了晶体结构。
