(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 | 84396-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 84396-27-0
• 化学式: C₃₈H₅₁BrO₂₅
• 分子量: 987.712
• InChiKey: MXIJJOBJUPJMSU-KKNHDGRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  309.15
• 氢给体数：
  0.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  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 phenyl 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
• 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)-1,2,4,6-tetra-O-acetyl-D-glucopyranose 在 氢溴酸 作用下， 反应 0.5h， 以98%的产率得到(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
  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

• The Synthesis of Active-Site Directed Inhibitors of Some β-Glucan Hydrolases
  作者：EB Rodriguez、RV Stick

  DOI：10.1071/ch9900665

  日期：——

  The 2,3-epoxypropyl, 3,4-epoxybutyl and 4,5-epoxypentyl β-glycosides of D-glucose, cellobiose and laminaribiose have been prepared. As well, the 4,5-epoxypentyl β-glycosides of cellotriose, laminaritriose and two other trisaccharides have been synthesized. 3,4-Epoxybutyl β-cellobioside has also been prepared with a 14C-label in the cellobiose residue.

  制备出了 D-葡萄糖、纤维生物糖和片状生物糖的 2,3-环氧丙基、3,4-环氧丁基和 4,5-环氧戊基 β-糖苷。此外，还合成了纤维三糖、片状三糖和另外两种三糖的 4,5-环氧戊基 β-糖苷。此外，还制备了 3,4-环氧丁基 β-纤维二糖苷，并在纤维二糖残基中添加了 14C 标记。
• Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases
  作者：Namrata Jain、Kazune Tamura、Guillaume Déjean、Filip Van Petegem、Harry Brumer

  DOI：10.1021/acschembio.1c00063

  日期：2021.10.15
• Expeditious synthesis of a new hexasaccharide using transglycosylation reaction catalyzed by Bacillus (1→3),(1→4)-β-d-glucan 4-glucanohydrolase
  作者：Josep-Lluı́s Viladot、Bruce Stone、Hugues Driguez、Antoni Planas

  DOI：10.1016/s0008-6215(98)00212-2

  日期：1998.9

  Enzymatic hydrolysis of barley (1-->3),(1-->4)-beta-D-glucan using a recombinant (1-->3),(1-->4)-beta-glucanase from Bacillus licheniformis gives Glc beta 4Glc beta 3Glc isolated after acetylation in 49% yield. Conventional treatment produced the corresponding beta-fluoride which was carefully de-O-acetylated. A transglycosylation reaction with this substrate, catalyzed by the title enzyme, gave Glc beta 4Glc beta 3Glc beta 4Glc beta 4Glc beta 3Glc in 20% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.