3,4-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside | 215776-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5R,6R)-2-(3,4-dinitrophenoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 215776-09-3
• 化学式: C₂₄H₃₄N₂O₂₀
• 分子量: 670.535
• InChiKey: ITFWRPUVKKCKNK-DLLNSMGHSA-N

物化性质

• 沸点：
  1059.1±65.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  349
• 氢给体数：
  10
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  3,4-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside 在 1,3-1,4-glucanase (from Bacillus licheniformis) 、 水 作用下， 以 水 为溶剂， 生成 3,4-二硝基苯酚 、 O-β-D-glucopyranosyl-(1-4)-O-β-D-glucopyranosyl-(1-3)-β-D-glucose
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 在 甲醇 、 sodium hydroxide 、 sodium methylate 、 苄基三乙基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,4-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x

文献信息

• Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases
  作者：Antoni Planas、Mireia Abel、Óscar Millet、Josep Palasi、Cristina Pallarés、Josep-Lluı́s Viladot

  DOI：10.1016/s0008-6215(98)00175-x

  日期：1998.8

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.