(S)-4-氰基-3-羟基丁酰胺 | 158008-69-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-4-氰基-3-羟基丁酰胺
• 英文名称: 3-hydroxybutyric acid
• 英文别名: 4-Cyano-3-hydroxybutanamide
• CAS: 158008-69-6
• 化学式: C₅H₈N₂O₂
• 分子量: 128.131
• InChiKey: JGNICYPMHKZAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (苯基硫醇)乙酰氯 、 (S)-4-氰基-3-羟基丁酰胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Phenylsulfanyl-acetic acid 1-carbamoylmethyl-2-cyano-ethyl ester
  参考文献：
  名称：

  方便的光学纯3-羟基戊二酸衍生物的制备

  摘要：

  由（L）-半胱氨酸与3-羟基戊二醛缩合的缩合产生的非对映体单酰胺已通过色谱分离，然后在几个步骤中转化为4-氰基-3-羟基丁酸的（+）或（-）甲酯。

  DOI：

  10.1016/s0040-4039(00)73032-2
• 作为产物：
  描述：

  3-羟基戊二腈 在 bacterial isolate 作用下， 以 aq. phosphate buffer 为溶剂， 生成 4-cyano-3-hydroxybutyric acid 、 (S)-4-氰基-3-羟基丁酰胺
  参考文献：
  名称：

  A high throughput screening strategy for the assessment of nitrile-hydrolyzing activity towards the production of enantiopure β-hydroxy acids

  摘要：

  Nitrile hydrolysing enzymes have found wide use in the pharmaceutical industry for the production of fine chemicals. This work presents a strategy that facilitates the rapid identification of bacterial isolates demonstrating nitrile hydrolysing activity. The strategy incorporates toxicity, starvation and induction studies along with subsequent colorimetric screening for activity, further focusing the assessment towards the substrates of interest. This high-throughput strategy uses a 96 well plate system, and has enabled the rapid biocatalytic screening of 256 novel bacterial isolates towards beta-hydroxynitriles. Results demonstrate the strategy's potential to rapidly assess a variety of beta-hydroxynitriles including aliphatic, aromatic and dinitriles. A whole cell catalyst Rhodococcus erythropolis SET1 was identified and found to catalyse the hydrolysis of 3-hydroxybutyronitrile with remarkably high enantioselectivity under mild conditions, to afford (S)-3-hydroxybutyric acid in 42% yield and >99.9% ee. The biocatalytic capability of this strain including the variation of parameters such as temperature and time were further investigated and all results indicate the presence of a highly enantioselective if not enantiospecific nitrilase enzyme within the microbial whole cell. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.08.001

文献信息

• A mild hydration of nitriles into amides
  作者：P. Breuilles、R. Leclerc、D. Uguen

  DOI：10.1016/s0040-4039(00)76229-0

  日期：1994.2

  Stirring mixtures of β-hydroxynitriles with manganese dioxide, deposited onto silica gel for a few days at room temperature resulted in the formation of the corresponding amides in fair to good yields. The unprecedented conversion of 3-hydroxyglutarodinitrile into the corresponding monoamide has been performed by this methodology.

  在室温下将几天内沉积在硅胶上的β-羟基腈与二氧化锰的混合物进行搅拌，导致以适当的收率形成了相应的酰胺。通过这种方法已经完成了3-羟基戊二腈向相应的单酰胺的前所未有的转化。
• A high throughput screening strategy for the assessment of nitrile-hydrolyzing activity towards the production of enantiopure β-hydroxy acids
  作者：Tracey M. Coady、Lee V. Coffey、Catherine O‘Reilly、Erica B. Owens、Claire M. Lennon

  DOI：10.1016/j.molcatb.2013.08.001

  日期：2013.12

  Nitrile hydrolysing enzymes have found wide use in the pharmaceutical industry for the production of fine chemicals. This work presents a strategy that facilitates the rapid identification of bacterial isolates demonstrating nitrile hydrolysing activity. The strategy incorporates toxicity, starvation and induction studies along with subsequent colorimetric screening for activity, further focusing the assessment towards the substrates of interest. This high-throughput strategy uses a 96 well plate system, and has enabled the rapid biocatalytic screening of 256 novel bacterial isolates towards beta-hydroxynitriles. Results demonstrate the strategy's potential to rapidly assess a variety of beta-hydroxynitriles including aliphatic, aromatic and dinitriles. A whole cell catalyst Rhodococcus erythropolis SET1 was identified and found to catalyse the hydrolysis of 3-hydroxybutyronitrile with remarkably high enantioselectivity under mild conditions, to afford (S)-3-hydroxybutyric acid in 42% yield and >99.9% ee. The biocatalytic capability of this strain including the variation of parameters such as temperature and time were further investigated and all results indicate the presence of a highly enantioselective if not enantiospecific nitrilase enzyme within the microbial whole cell. (C) 2013 Elsevier B.V. All rights reserved.
• A convenient preparation of optically pure 3-hydroxyglutaric acid derivatives
  作者：R. Leclerc、D. Uguen

  DOI：10.1016/s0040-4039(00)73032-2

  日期：1994.3

  The diastereomeric monoamides resulting from condensation of (L)-cysteine with 3-hydroxyglutarodinitrile have been separted by chromatography then transformed in a few steps into either (+) or (-) methyl ester of 4-cyano-3-hydroxybutyric acid.

  由（L）-半胱氨酸与3-羟基戊二醛缩合的缩合产生的非对映体单酰胺已通过色谱分离，然后在几个步骤中转化为4-氰基-3-羟基丁酸的（+）或（-）甲酯。