(R)-(1-phenylethyl)-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(1-phenylethyl)-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[(1R)-1-phenylethoxy]oxane-3,4,5-triol
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: FVJSVPNFQKQHOB-MWQIOUDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-(+)-1-苯基乙醇 、 4-硝基苯基-D-吡喃葡糖苷 在 beta-galactosidase 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 生成 (R)-(1-phenylethyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Effective transgalactosylation catalysed by a lipid-coated β-D-galactosidase in organic solvents

  摘要：

  A lipid-coated beta-D-galactosidase was prepared, which was soluble in most organic solvents such as diisopropyl ether, 2,2,4-trimethylpentane and benzene, but insoluble in aqueous solution. It could act as an efficient transgalactosylation catalyst for various hydrophobic alcohols with p-nitrophenyl beta-D-galactopyranoside in dry diisopropyl ether. When a native beta-D-galactosidase was used in aqueous solution containing acetonitrile for the same reaction, the yield of the transgalactosylation was low due to the predominant process of hydrolysis. The enzyme activity for the galactosylation depended on coating lipid molecules, the origin of the enzyme used, the reaction's organic solvents and the chemical structures of the acceptor alcohols.

  DOI：

  10.1039/p19960002861

文献信息

• Diastereoselective synthesis of (R)-(alkyl)-β-d-galactopyranoside by using β-galactosidase (Aspergillus oryzae) in low-water media
  作者：Abir B. Majumder、Bhupender Singh、Munishwar N. Gupta

  DOI：10.1016/j.bmcl.2007.11.006

  日期：2008.1

  beta-galactosidase under low water conditions (temperature 55 degrees C, reaction time of 4 h) gave enantioselectivity, E > 1000 for the stereoselective synthesis of (R)-(1-phenylethyl)-beta-D-galactopyranoside, starting from racemic 1-phenylethanol and D-galactose. For racemic 2-octanol also, EPRP worked better. Under similar conditions, (R)-(2-octyl)-beta-D-galactopyranoside was formed with an enantioselectivity

  β-半乳糖苷酶（来自米曲霉）制剂。通过用正丙醇沉淀除去大量水而获得的EPRP（酶沉淀并用丙醇冲洗）显示出比冻干粉更高的生物活性。FT-IR研究证实，EPRP比冻干形式更好地保留了天然结构的α-螺旋含量。在低水条件（温度55摄氏度，反应时间4小时）下使用此配方的β-半乳糖苷酶可获得立体选择性E> 1000，用于立体选择性合成（R）-（1-苯乙基）-β-D-吡喃半乳糖苷，从外消旋的1-苯基乙醇和D-半乳糖开始。对于外消旋的2-辛醇，EPRP的效果也更好。在类似条件下，形成（R）-（2-辛基）-β-D-吡喃半乳糖苷，对映选择性E = 38。
• Effective transgalactosylation catalysed by a lipid-coated β-<scp>D</scp>-galactosidase in organic solvents
  作者：Yoshio Okahata、Toshiaki Mori

  DOI：10.1039/p19960002861

  日期：——

  A lipid-coated beta-D-galactosidase was prepared, which was soluble in most organic solvents such as diisopropyl ether, 2,2,4-trimethylpentane and benzene, but insoluble in aqueous solution. It could act as an efficient transgalactosylation catalyst for various hydrophobic alcohols with p-nitrophenyl beta-D-galactopyranoside in dry diisopropyl ether. When a native beta-D-galactosidase was used in aqueous solution containing acetonitrile for the same reaction, the yield of the transgalactosylation was low due to the predominant process of hydrolysis. The enzyme activity for the galactosylation depended on coating lipid molecules, the origin of the enzyme used, the reaction's organic solvents and the chemical structures of the acceptor alcohols.