异弗罗里多苷 | 4649-46-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 异弗罗里多苷
• 英文名称: 1-O-α-D-galactopyranosylglycerol
• 英文别名: 2-O-D-glycerol-α-D-galactoside；D‑isofloridoside；D-isofloridoside；isofloridoside；1-O-α-D-galactosylglycerol；floridoside；(2S,3R,4S,5R,6R)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 4649-46-1
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: NHJUPBDCSOGIKX-KJUJXXMOSA-N

物化性质

• 熔点：
  134-135 °C(Solv: ethanol (64-17-5))
• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  异弗罗里多苷 在 α-galactosidase 作用下， 反应 0.08h， 生成 D-吡喃葡萄糖 、 甘油
  参考文献：
  名称：

  Poterioochromonas malhamensis 的α-半乳糖苷酶

  摘要：

  摘要 在 Poterioochromonas malhamensis 的无细胞提取物中，α-半乳糖苷酶（α-d-半乳糖苷半乳糖水解酶，EC 3.2.1.22）在 pH 8 下稳定。该酶的最适 pH 为 7。该酶通过色谱纯化 10 倍涉及 DEAE-纤维素、羟基磷灰石和 Sephadex G-200 的步骤。蔗糖密度梯度离心的表观MW为360 000。使酶进行聚丙烯酰胺凝胶电泳后，所有活性都丧失了。检查了酶的底物特异性并确定了一些动力学值。该酶对异氟烷苷显示出异常的活性曲线。

  DOI：

  10.1016/0031-9422(81)85216-8
• 作为产物：
  描述：

  (R,S)-2,3-epoxypropyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 异弗罗里多苷
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• A synthesis of diastereomeric isofloridoside
  作者：Ross C. Beier、Bradford P. Mundy、Gary A. Strobel

  DOI：10.1016/s0008-6215(00)80759-4

  日期：1981.6
• Enzymatic properties and transglycosylation of α-galactosidase from Penicillium oxalicum SO
  作者：Masahiro Kurakake、Youichirou Moriyama、Riku Sunouchi、Shinya Nakatani

  DOI：10.1016/j.foodchem.2010.10.095

  日期：2011.5

  Penicillium oxalicum SO alpha-galactosidase demonstrated weak hydrolysing activity but a high rate of transglycosylation in the reaction with melibiose, where the major product was 6-alpha-galactosyl melibiose. The transfer ratio was 83.6% and was maintained over a long reaction time of 80 h. The molecular weight was estimated to be 124,000 by SDS-PAGE. The optimal pH was similar to 3 and a stable pH, with a range of 2.4-9.5, was found. The optimal temperature was similar to 60 degrees C and the activity was stable below 60 degrees C. With respect to acceptor specificity, mono-alcohols, sugar alcohols and sugars were poor acceptors, but the di-alcohol ethylene glycol and the tri-alcohol glycerin were good acceptors. The percentage of transglycosylation to glycerin increased up to 41.7%, as that to melibiose decreased, with the initial glycerin concentration of 40%. The production of alpha-D-galactosylglycerol was 293 mg for each gram of melibiose used by the enzymatic reaction. (C) 2010 Elsevier Ltd. All rights reserved.