1-methylpropyl β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methylpropyl β-D-galactopyranoside
• 英文别名: sec-Butyl β-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-butan-2-yloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: SPMHDJVTXLHOTJ-WUXYXMPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-methylpropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 1-甲基吡咯烷 作用下， 以 甲醇 为溶剂， 以58%的产率得到1-methylpropyl β-D-galactopyranoside
  参考文献：
  名称：

  Werschkun, Barbara; Koenig, Wilfried A.; Kren, Vladimir, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2459 - 2466

  摘要：

  DOI：

文献信息

• A Facile Transgalactosylation catalyzed by a Lipid-Coated β-<i>D</i>-Galactosidase in the Water-Organic Two Phases
  作者：Toshiaki Mori、Sanae Fujita、Yoshio Okahata

  DOI：10.1246/cl.1997.73

  日期：1997.1

  A lipid-coated β-D-galactosidase could act as an efficient catalyst for transgalactosylation in the water-organic two phases: both the hydrophobic lipid-coated enzyme and alcohols were solubilized in isopropyl ether and mixed with an aqueous solution of lactose (a galactosyl donor). When a native β-D-galactosidase was employed for the same reaction, neither the transgalactosylation nor the hydrolysis reaction proceeded due to the deactivation of the enzyme at the interface.

  一种脂质包被的β-D-半乳糖苷酶可以作为水-有机两相中转半乳糖基化的高效催化剂：脂肪性脂质包被的酶和醇在异丙醚中被溶解，并与乳糖（半乳糖基供体）的水溶液混合。当使用天然的β-D-半乳糖苷酶进行相同反应时，由于酶在界面处失活，既未发生转半乳糖基化反应，也未发生水解反应。
• 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.
• Transglycosylation in a two-phase aqueous-organic system with catalysis by a lipid-coated β-d-galactosidase
  作者：Toshiaki Mori、Sanae Fujita、Yoshio Okahata

  DOI：10.1016/s0008-6215(96)00298-4

  日期：1997.2

  A lipid-coated beta-D-galactosidase was prepared in which the enzyme surface is covered with a lipid monolayer and two long alkyl lipophilic tails serve to solubilize the enzyme in organic solvents. In a two-phase aqueous-organic system, a lipid-coated enzyme exists in the organic (2-propyl ether) phase and acts as an efficient transgalactosylation catalyst for various hydrophobic alcohols with lactose in the aqueous buffer solution. When a native beta-D-galactosidase was employed in the two-phase system, neither the transgalactosylation nor the hydrolysis reaction proceeded due to denaturation of the enzyme at the interface, Effects of coating lipid molecules, origins of enzymes, reaction in organic solvents, and chemical structures of acceptor alcohols on the transgalactosylation catalyzed by the lipid-coated enzyme were studied. This system could also be applied in a large-scale synthesis on the 0.1-1 g scale. (C) 1997 Elsevier Science Ltd.
• Werschkun, Barbara; Koenig, Wilfried A.; Kren, Vladimir, Journal of the Chemical Society. Perkin transactions I, 1995, # 19, p. 2459 - 2466
  作者：Werschkun, Barbara、Koenig, Wilfried A.、Kren, Vladimir、Thiem, Joachim

  DOI：——

  日期：——