2,4-dinitrophenyl 2-deoxy-β-D-mannopyranoside | 262607-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dinitrophenyl 2-deoxy-β-D-mannopyranoside
• 英文别名: 2,4-dinitrophenyl-2-fluoro-2-deoxy-β-D-mannopyranoside；2,4-dinitrophenyl 2-deoxy-2-fluoro-β-D-mannopyranoside；2,4-Dinitrophenyl 2-Deoxy-2-Fluoro-Beta-D-Mannopyranoside；(2R,3S,4S,5S,6S)-6-(2,4-dinitrophenoxy)-5-fluoro-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 262607-46-5
• 化学式: C₁₂H₁₃FN₂O₉
• 分子量: 348.242
• InChiKey: UFSBFVZQJZMIOU-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Α-D-氟代吡喃甘露糖 、 2,4-dinitrophenyl 2-deoxy-β-D-mannopyranoside 在 Man₂a Glu 519 Ser 作用下， 以 various solvent(s) 为溶剂， 生成 (2S,3S,4S,5S,6R)-2-{(2R,3S,4R,5S,6S)-6-[(2R,3S,4S,5S,6S)-6-(2,4-Dinitro-phenoxy)-5-fluoro-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 、 (2S,3S,4S,5S,6R)-2-{(2R,3S,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-(2,4-Dinitro-phenoxy)-3-fluoro-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  β-Mannosynthase: Synthesis ofβ-Mannosides with a Mutantβ-Mannosidase

  摘要：

  Engineering enzymes: The glutamic acid nucleophile of a retaining β-mannosidase has been replaced with a serine residue to form a β-mannosynthase. When the new enzyme is provided with an α-mannosyl fluoride donor and an appropriate acceptor, β-mannoside linkages are synthesized. Remarkably, α-mannosyl fluoride can be generated in situ by providing the mannosynthase with excess fluoride ion.

  DOI：

  10.1002/1521-3773(20010119)40:2<417::aid-anie417>3.0.co;2-v
• 作为产物：
  描述：

  2,4-dinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-mannopyranoside 在 甲醇 、 乙酰氯 作用下， 反应 48.0h， 以87%的产率得到2,4-dinitrophenyl 2-deoxy-β-D-mannopyranoside
  参考文献：
  名称：

  Structure of the Michaelis complex of β-mannosidase, Man2A, provides insight into the conformational itinerary of mannoside hydrolysis

  摘要：

  δ-甘露糖苷酶 Man2A 的 Michaelis 复合物显示出向 1S5 构象的变形，这为越来越多的证据支持通过舟形构象进行催化增添了依据。

  DOI：

  10.1039/b902240f

文献信息

• The Role of Sugar Substituents in Glycoside Hydrolysis
  作者：Mark N. Namchuk、John D. McCarter、Adam Becalski、Trevor Andrews、Stephen G. Withers

  DOI：10.1021/ja992044h

  日期：2000.2.1

  used to probe the mechanism of spontaneous β-glycoside hydrolysis. Their relative rates of hydrolysis followed the order 2-deoxy > 4-deoxy > 3-deoxy ≈ 6-deoxy > parent > 6-deoxy-6-fluoro > 3-deoxy-3-fluoro > 4-deoxy-4-fluoro > 2-deoxy-2-fluoro. Hammett correlations of the pH-independent hydrolysis rates of each of the 6-, 4-, 3-, and 2-position substituted glycosides with the σI value for the sugar

  合成了一系列单取代的脱氧和脱氧氟 2,4-二硝基苯基 (DNP) β-d-吡喃糖苷，并用于探索自发 β-糖苷水解的机制。它们的相对水解速率顺序为 2-脱氧 > 4-脱氧 > 3-脱氧 ≈ 6-脱氧 > 母体 > 6-脱氧-6-氟 > 3-脱氧-3-氟 > 4-脱氧-4-氟 > 2-脱氧-2-氟。6 位、4 位、3 位和 2 位取代糖苷的 pH 无关水解速率与糖环取代基的 σI 值的哈米特相关性是线性的（r = 0.95 至 0.999，ρI = -2.2到-10.7），这与水解速率主要取决于对缺电子过渡态的场效应。正如 Kirkwood-Westheimer 模型预测的那样，DNP 糖苷的相对水解速率可以根据类氧碳鎓离子过渡态的稳定性进行合理化。一系列内水解速率的主要决定因素似乎是环取代基的场效应……