1-methoxy propane 1,2-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxy propane 1,2-diol
• 英文别名: pyruvic aldehyde methyl acetal；1-methoxy-1,2-propane diol；methoxy-1,2-propanediol；(S)-Methoxypropane-1,2-diol；methoxypolypropylene glycol；Methoxypropanol-2-ol；1-methoxypropane-1,2-diol
• 化学式: C₄H₁₀O₃
• 分子量: 106.122
• InChiKey: OEYNWAWWSZUGDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙酮酸甲酯 在 2,3,4,5,6-pentahydroxy-hexanal 、 Bacillus subtilis glucose dehydrogenase 、 Saccharomyces cerevisiae dehydrogenase Gre₂p 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 生成 1-methoxy propane 1,2-diol
  参考文献：
  名称：

  Highly efficient and stereoselective biosynthesis of (2S,5S)-hexanediol with a dehydrogenase from Saccharomyces cerevisiae

  摘要：

  高光学纯度(2S,5S)-己二醇作为一种多用途的构建单元，可用于生产各种精细化学品和药物。在工业和商业规模上，目前通过面包酵母介导的2,5-己二酮还原反应制备该二醇。然而，这一过程存在空间时间产率不足的问题，约为每天每升4克(2S,5S)-己二醇。因此，需要开发一种新的合成路线，以实现更高的体积生产率。为此，通过纯化至均一性并随后进行MALDI-TOF质谱分析，鉴定了面包酵母中负责2,5-己二酮还原的酶。结果显示，与缺乏对2,5-己二酮活性的Gre2p缺失株相比，脱氢酶Gre2p主要负责该二酮的还原。利用重组酶进行生物还原，可获得转化率>99%且对映体过量>99.9%的(2S,5S)-己二醇。此外，该二醇的体积生产率达到了前所未有的70 g L−1 d−1 (2S,5S)-己二醇。米氏动力学研究表明，Gre2p能够催化2,5-己二酮的还原和(2S,5S)-己二醇的氧化，但还原的催化效率高出三倍。此外，研究了该酶对其他酮类化合物（包括更多的二酮）的还原能力，发现其应用可扩展到α-二酮和醛。

  DOI：

  10.1039/b920869k

文献信息

• Zeolite H-USY for the production of lactic acid and methyl lactate from C3-sugars
  作者：Ryan M. West、Martin Spangsberg Holm、Shunmugavel Saravanamurugan、Jianmin Xiong、Zachary Beversdorf、Esben Taarning、Claus Hviid Christensen

  DOI：10.1016/j.jcat.2009.10.023

  日期：2010.1

  Lactic acid is an interesting platform chemical with many promising applications. This includes the use as a building block for the production of biodegradable plastics and environmentally friendly solvents. A study of the liquid-phase conversion of the triose-sugars, glyceraldehyde and dihydroxyacetone directly to methyl lactate and lactic acid catalyzed by inexpensive commercially available zeolites is presented. One particular zeolite, H-USY (Si/Al = 6) is shown to be quite active with near quantitative yields for this isomerization. Deactivation of the H-USY-zeolite was studied by correlating the catalytic activity to data obtained by TPO, XRD, N-2-sorption, and NH3-TPD on fresh and used catalysts. Coking and irreversible framework damage occurs when lactic acid is produced under aqueous conditions. In methanol, methyl lactate is produced and catalyst deactivation is suppressed. Additionally, reaction rates for the formation of methyl lactate in methanol are almost an order of magnitude higher as compared to the rate of lactic acid formation in water. (c) 2009 Elsevier Inc. All rights reserved.