(S)-2-hydroxy-valeric acid amide | 66461-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-hydroxy-valeric acid amide
• 英文别名: (S)-2-Hydroxy-valeriansaeure-amid；(2S)-2-hydroxypentanamide
• CAS: 66461-72-1
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: DPSHJKZKKFYEHL-BYPYZUCNSA-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：

  (2S)-2-Hydroxypentanoic acid methyl ester 在 甲醇 、 氨 作用下， 生成 (S)-2-hydroxy-valeric acid amide
  参考文献：
  名称：

  USTILAGINALES 的生物化学：IV。一些β-羟基酸的构型和β-酮酸的生物还原

  摘要：

  β-酮-正己酸和β-酮-正-辛酸的植物化学还原产生相应的D-β-羟基酸。该观察结果与 β-酮丁酸生物还原为 L-β-羟基丁酸形成对比。讨论了分配上述配置的基础。L-α-羟基-n-戊酰胺用氢化铝锂还原，产物乙酰化得到L-1-乙酰氨基-2-乙酰氧基戊烷。后一种化合物的对映形式是通过 D-β-羟基-n-己酰肼的 Curtius 降解获得的。分配给 β-羟基-n-辛酸的构型基于同源化合物旋光度的 Levene-Marker 规则。因此，从乌司提酸衍生的β-羟基-正己酸和β-羟基-正-辛酸被证明属于L-系列。

  DOI：

  10.1139/v51-076

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.
• BIOCHEMISTRY OF THE USTILAGINALES: IV. THE CONFIGURATIONS OF SOME β–HYDROXYACIDS AND THE BIOREDUCTION OF β–KETOACIDS
  作者：R. U. Lemieux、Jacques Giguere

  DOI：10.1139/v51-076

  日期：1951.8.1

  The basis for the assignment of the above configurations is discussed. L-α-Hydroxy-n-valeramide was reduced with lithium aluminium hydride and the product was acetylated to yield L-1-acetamido-2-acetoxypentane. The enantiomorphic form of the latter compound was obtained through the Curtius degradation of D-β-hydroxy -n-caprohydrazide. The configurations assigned to the β-hydroxy-n-caprylic acids are

  β-酮-正己酸和β-酮-正-辛酸的植物化学还原产生相应的D-β-羟基酸。该观察结果与 β-酮丁酸生物还原为 L-β-羟基丁酸形成对比。讨论了分配上述配置的基础。L-α-羟基-n-戊酰胺用氢化铝锂还原，产物乙酰化得到L-1-乙酰氨基-2-乙酰氧基戊烷。后一种化合物的对映形式是通过 D-β-羟基-n-己酰肼的 Curtius 降解获得的。分配给 β-羟基-n-辛酸的构型基于同源化合物旋光度的 Levene-Marker 规则。因此，从乌司提酸衍生的β-羟基-正己酸和β-羟基-正-辛酸被证明属于L-系列。