o-nitrophenyl β-D-[1-13C]galactopyranoside | 864933-71-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-nitrophenyl β-D-[1-13C]galactopyranoside
• 英文别名: Onpg-13C；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(2-nitrophenoxy)(613C)oxane-3,4,5-triol
• CAS: 864933-71-1
• 化学式: C₁₂H₁₅NO₈
• 分子量: 302.242
• InChiKey: KUWPCJHYPSUOFW-AHIYVFTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.23
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142.52
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  o-nitrophenyl β-D-[1-13C]galactopyranoside 、 甲基 Β-D-吡喃葡萄糖苷 生成 methyl β-D-[1-13C]galactopyranosyl-(1->6)-β-D-glucopyranoside 、 methyl β-D-[1-13C]galactopyranosyl-(1->3)-β-D-glucopyranoside
  参考文献：
  名称：

  Methyl β-allolactoside [methyl β-D-galactopyranosyl-(1→6)-β-D-glucopyranoside] monohydrate

  摘要：

  Methyl beta-allolactoside [methyl beta-d-galactopyranosyl-(1 -> 6)-beta-D-glucopyranoside], (II), was crystallized from water as a monohydrate, C(13)H(24)O(11 center dot)H(2)O. The beta Galp and beta Glcp residues in (II) assume distorted (4)C(1) chair conformations, with the former more distorted than the latter. Linkage conformation is characterized by phi ' (C2(Gal)-C1(Gal)-O1(Gal)-C6(Glc)), psi ' (C1(Gal)-O1(Gal)-C6(Glc)-C5(Glc)) and omega (C4(Glc)-C5(Glc)-C6(Glc)-O1(Gal)) torsion angles of 172.9 (2), -117.9 (3) and -176.2 (2)degrees, respectively. The psi ' and omega values differ significantly from those found in the crystal structure of beta-gentiobiose, (III) [Rohrer et al. (1980). Acta Cryst. B36, 650-654]. Structural comparisons of (II) with related disaccharides bound to a mutant beta-galactosidase reveal significant differences in hydroxymethyl conformation and in the degree of ring distortion of the beta Glcp residue. Structural comparisons of (II) with a DFT-optimized structure, (II(C)), suggest a link between hydrogen bonding, pyranosyl ring deformation and linkage conformation.

  DOI：

  10.1107/s0108270109042310
• 作为产物：
  描述：

  <1-13C>-β-D-galactopyranose 、 硝苯酚 以30%的产率得到o-nitrophenyl β-D-[1-13C]galactopyranoside
  参考文献：
  名称：

  Methyl β-allolactoside [methyl β-D-galactopyranosyl-(1→6)-β-D-glucopyranoside] monohydrate

  摘要：

  Methyl beta-allolactoside [methyl beta-d-galactopyranosyl-(1 -> 6)-beta-D-glucopyranoside], (II), was crystallized from water as a monohydrate, C(13)H(24)O(11 center dot)H(2)O. The beta Galp and beta Glcp residues in (II) assume distorted (4)C(1) chair conformations, with the former more distorted than the latter. Linkage conformation is characterized by phi ' (C2(Gal)-C1(Gal)-O1(Gal)-C6(Glc)), psi ' (C1(Gal)-O1(Gal)-C6(Glc)-C5(Glc)) and omega (C4(Glc)-C5(Glc)-C6(Glc)-O1(Gal)) torsion angles of 172.9 (2), -117.9 (3) and -176.2 (2)degrees, respectively. The psi ' and omega values differ significantly from those found in the crystal structure of beta-gentiobiose, (III) [Rohrer et al. (1980). Acta Cryst. B36, 650-654]. Structural comparisons of (II) with related disaccharides bound to a mutant beta-galactosidase reveal significant differences in hydroxymethyl conformation and in the degree of ring distortion of the beta Glcp residue. Structural comparisons of (II) with a DFT-optimized structure, (II(C)), suggest a link between hydrogen bonding, pyranosyl ring deformation and linkage conformation.

  DOI：

  10.1107/s0108270109042310