α-D-glucopyranosyl-(1→4)-4D-myo-inositol | 136457-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1→4)-4D-myo-inositol
• 英文别名: α-D-glucopyranosyl-(1->4)-4D-myo-inositol
• CAS: 136457-84-6
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: VCWMRQDBPZKXKG-CTUWURKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.01
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  200.53
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranosyl-(1→4)-4D-myo-inositol 、 苯甲酰氯 在 吡啶 作用下， 20.0~90.0 ℃ 、89.63 kPa 条件下， 以75%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1->4)-1,2,3,5,6-penta-O-benzoyl-4D-myo-inositol
  参考文献：
  名称：

  Stereoselective enzymatic synthesis of monoglucosyl-myo-inositols with in vivo anti-inflammatory activity

  摘要：

  The monoglucosyl-inositols alpha-D-glucopyranosyl-(1 -> 4)-4D-myo-inositol 3 and alpha-D-glucopyranosyl-(1 -> 1)-1D-myo-inositol 4 were synthesized by a combined enzymatic transglucosylation and hydrolysis strategy, using cyclodextrin glucosyl transferase (CGTase) from Thermoanaerobacter sp, followed by hydrolysis with Aspergillus niger glucoamylase The glucosides were separated by preparative HPLC and fully characterized by extensive 1D and 2D NMR studies. The structure of the regioisomer 4 was confirmed by X-ray crystallography of its perbenzoylated derivative 4a Both isomers demonstrated in vivo anti-inflammatory activity at comparative levels to corticosterone on mouse ear oedema induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and in rat hind paw oedema Induced by carrageenan (c) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.12.009
• 作为产物：
  描述：

  Inositol 、 β-环糊精 在 Thermoanaerobacter sp. cyclodextrin glucosyl transferase 、 Aspergillus niger glucoamylase 、 水 作用下， 以 aq. phosphate buffer 为溶剂， 反应 48.0h， 生成 α-D-glucopyranosyl-(1→4)-1D-myo-inositol 、 α-D-glucopyranosyl-(1→4)-4D-myo-inositol
  参考文献：
  名称：

  Regioselective glucosylation of inositols catalyzed by Thermoanaerobacter sp. CGTase

  摘要：

  Monoglucosylated products of L-chiro-, D-chiro-, muco-, and allo-inositol were synthesized by regioselective alpha-D-glucosylation with cyclodextrin glucosyl transferase from Thermoanaerobacter sp. after hydrolysis of by products with Aspergillus niger glucoamylase. While the reactions carried out with D-chiro-, muco-, and allo-inositol resulted in the regioselective formation of monoglucosylated products, two products were obtained in the reaction with L-chiro-inositol. Through the structural characterization of the glucosylated inositols here we demonstrated that the selectivity observed in the glucosylation of several inositols by Thermoanaerobacter sp. CGTase, is analogous to the specificity observed for the glucosylation of beta-D-glucopyranose and equivalent glucosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.002