(2R)-2-hydroxypentanamide | 1186526-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-hydroxypentanamide
• CAS: 1186526-75-9
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: DPSHJKZKKFYEHL-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氢氰酸 、 正丁醛 在 (S)-hydroxynitrile lyase from Manihot esculenta 、 nitrile hydratase from Nitriliruptor alkaliphilus 、 水 作用下， 生成 (S)-2-hydroxy-valeric acid amide 、 (2R)-2-hydroxypentanamide
  参考文献：
  名称：

  固定化的氧化硝化酶和腈水合酶的一锅双酶级联反应合成脂肪族（S）-α-羟基羧酸酰胺

  摘要：

  Abstractmagnified imageA one‐pot bienzymatic cascade combining a hydroxynitrile lyase (Manihot esculenta, E.C. 4.1.2.10) and a nitrile hydratase (Nitriliruptor alkaliphilus, E.C. 4.2.1.84) for the synthesis of enantiopure aliphatic α‐hydroxycarboxylic amides from aldehydes is described. Both enzymes were immobilised as cross‐linked enzyme aggregates (CLEAs). Stability tests show that the nitrile hydratase CLEAs are sensitive to water‐immiscible organic solvents as well as to aldehydes and hydrogen cyanide (HCN), but are remarkably stable and show useful activity in acidic aqueous environments of pH 4–5. The cascade reactions are consequently carried out by using a portionwise feed of HCN and moderate concentrations of aldehyde in acidic aqueous buffer to suppress the uncatalysed hydrocyanation background reaction. After optimisation, this method was used to synthesise five different kinds of aliphatic α‐hydroxycarboxylic amides from the corresponding aldehydes with good yields and with enantiomeric purities comparable to those obtained for the α‐hydroxynitriles in the microaqueous hydrocyanation using hydroxynitrile lyase and an excess of HCN.

  DOI：

  10.1002/adsc.200800625

文献信息

• Synthesis of Aliphatic (S)-α-Hydroxycarboxylic Amides using a One-Pot Bienzymatic Cascade of Immobilised Oxynitrilase and Nitrile Hydratase
  作者：Sander van Pelt、Fred van Rantwijk、Roger A. Sheldon

  DOI：10.1002/adsc.200800625

  日期：2009.2

  Abstractmagnified imageA one‐pot bienzymatic cascade combining a hydroxynitrile lyase (Manihot esculenta, E.C. 4.1.2.10) and a nitrile hydratase (Nitriliruptor alkaliphilus, E.C. 4.2.1.84) for the synthesis of enantiopure aliphatic α‐hydroxycarboxylic amides from aldehydes is described. Both enzymes were immobilised as cross‐linked enzyme aggregates (CLEAs). Stability tests show that the nitrile hydratase CLEAs are sensitive to water‐immiscible organic solvents as well as to aldehydes and hydrogen cyanide (HCN), but are remarkably stable and show useful activity in acidic aqueous environments of pH 4–5. The cascade reactions are consequently carried out by using a portionwise feed of HCN and moderate concentrations of aldehyde in acidic aqueous buffer to suppress the uncatalysed hydrocyanation background reaction. After optimisation, this method was used to synthesise five different kinds of aliphatic α‐hydroxycarboxylic amides from the corresponding aldehydes with good yields and with enantiomeric purities comparable to those obtained for the α‐hydroxynitriles in the microaqueous hydrocyanation using hydroxynitrile lyase and an excess of HCN.