(2S,3R)-2-aminopentane-1,3-diol | 1034360-31-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R)-2-aminopentane-1,3-diol
• CAS: 1034360-31-0
• 化学式: C₅H₁₃NO₂
• 分子量: 119.164
• InChiKey: PJBQQLVBENTUQY-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(2S,3R)-1,3-dihydroxypentan-2-yl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以100%的产率得到(2S,3R)-2-aminopentane-1,3-diol
  参考文献：
  名称：

  截短的二氢鞘氨醇类似物的杀真菌活性。

  摘要：

  确定了白色念珠菌和光滑念珠菌的二氢鞘氨醇（DHS），植物鞘氨醇（PHS）和五种短链DHS衍生物的最小杀真菌浓度（MFC）。在这方面，与天然DHS（即C18-DHS）相比，DHS的C15和C17同源物显示MFC降低了2到10倍。具有活性的DHS衍生物（即包含12、15、17或18个碳原子）诱导了白色念珠菌中活性氧物质（ROS）的积累。

  DOI：

  10.1016/j.bmcl.2008.05.067

文献信息

• A Multidisciplinary Approach Toward the Rapid and Preparative-Scale Biocatalytic Synthesis of Chiral Amino Alcohols: A Concise Transketolase-/ω-Transaminase-Mediated Synthesis of (2<i>S</i>,3<i>S</i>)-2-Aminopentane-1,3-diol
  作者：Mark E. B. Smith、Bing H. Chen、Edward G. Hibbert、Ursula Kaulmann、Kirsty Smithies、James L. Galman、Frank Baganz、Paul A. Dalby、Helen C. Hailes、Gary J. Lye、John M. Ward、John M. Woodley、Martina Micheletti

  DOI：10.1021/op900190y

  日期：2010.1.15

  Chiral amino alcohols represent an important class of value-added biochemicals and pharmaceutical intermediates. Chemical routes to such compounds are generally step intensive, requiring environmentally unfriendly catalysts and solvents. This work describes a multidisciplinary approach to the rapid establishment of biocatalytic routes to chiral aminodiols taking the original synthesis of (2S,3S)-2-aminopentane-1,3-diol as a specific example. An engineered variant of Escherichi coli transketolase (D469T) was used for the initial asymmetric ynthesis of (3S)-1,3-dihydroxypentan-2-one from the achiral substrates propanal and hydroxypyruvate. A bioinformatics led strategy was then used to identify and clone an omega-transaminase from Chromobacterium violaceum (DSM30191.) capable of converting the product of the transketolase-catalysed step to the required (2S,3S)-2-aminopentane-1,3-diol using isopropylamine as an inexpensive amine donor. Experiments; to characterize, optimize and model the kinetics of each reaction step were performed at the 1 mL scale using previously established automated microwell processing techniques. The microwell results, provided excellent predictions of the reaction kinetics when the. bioconversions were subsequently scaled up to preparative scales in batch stirred-tank reactors. The microwell methods thus provide process chemists and engineers with a valuable tool for the rapid and early evaluation of potential synthetic strategies. Overall, this work describes a concise and efficient biocatalytic route to chiral amino alcohols and illustrates an integrated multidisciplinary approach to bioconversion process design and scale-up.
• Fungicidal activity of truncated analogues of dihydrosphingosine
  作者：Karin Thevissen、Ulrik Hillaert、Els M.K. Meert、Kuen K. Chow、Bruno P.A. Cammue、Serge Van Calenbergh、Isabelle E.J.A. François

  DOI：10.1016/j.bmcl.2008.05.067

  日期：2008.7

  The minimal fungicidal concentration (MFC) of dihydrosphingosine (DHS), phytosphingosine (PHS), and five short-chain DHS derivatives was determined for Candida albicans and Candida glabrata. In this respect, a C15- and a C17-homologue of DHS showed a 2- to 10-fold decreased MFC as compared to native DHS (i.e. C18-DHS). DHS derivatives that were active, that is, comprising 12, 15, 17, or 18 carbon atoms

  确定了白色念珠菌和光滑念珠菌的二氢鞘氨醇（DHS），植物鞘氨醇（PHS）和五种短链DHS衍生物的最小杀真菌浓度（MFC）。在这方面，与天然DHS（即C18-DHS）相比，DHS的C15和C17同源物显示MFC降低了2到10倍。具有活性的DHS衍生物（即包含12、15、17或18个碳原子）诱导了白色念珠菌中活性氧物质（ROS）的积累。