2-aminopentane-1,3-diol hydrochloride | 1227946-82-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-aminopentane-1,3-diol hydrochloride
• CAS: 1227946-82-8
• 化学式: C₅H₁₃NO₂*ClH
• 分子量: 155.625
• InChiKey: CLRCXMUPCLOLDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.48
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 2-aminopentane-1,3-diol hydrochloride 在 吡啶 作用下， 生成 (2R,3R)-2-benzamido-3-hydroxypentanol dibenzoate ester 、 (2R,3S)-2-benzamido-3-hydroxypentanol dibenzoate ester 、 (2S,3R)-2-benzamido-3-hydroxypentanol dibenzoate ester 、 (2S,3S)-2-benzamido-3-hydroxypentanol dibenzoate ester
  参考文献：
  名称：

  A Multidisciplinary Approach Toward the Rapid and Preparative-Scale Biocatalytic Synthesis of Chiral Amino Alcohols: A Concise Transketolase-/ω-Transaminase-Mediated Synthesis of (2S,3S)-2-Aminopentane-1,3-diol

  摘要：

  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.

  DOI：

  10.1021/op900190y
• 作为产物：
  描述：

  2-benzylaminopentane-1,3-diol 在 盐酸 、 1% Pd/C 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 2-aminopentane-1,3-diol hydrochloride 、 2-aminopentane-1,3-diol hydrochloride
  参考文献：
  名称：

  A Multidisciplinary Approach Toward the Rapid and Preparative-Scale Biocatalytic Synthesis of Chiral Amino Alcohols: A Concise Transketolase-/ω-Transaminase-Mediated Synthesis of (2S,3S)-2-Aminopentane-1,3-diol

  摘要：

  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.

  DOI：

  10.1021/op900190y