4-cyanopentanoic acid ammonium salt

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-cyanopentanoic acid ammonium salt
• 英文别名: Azane;4-cyanopentanoic acid；azane;4-cyanopentanoic acid
• 化学式: C₆H₉NO₂*H₃N
• 分子量: 144.173
• InChiKey: LHLRJSBRGGHCFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyanopentanoic acid ammonium salt 在 镍 ammonium hydroxide 、 氢气 作用下， 以 水 为溶剂， 160.0 ℃ 、3.45 MPa 条件下， 反应 3.0h， 以59%的产率得到5-甲基-2-哌啶酮
  参考文献：
  名称：

  Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

  摘要：

  Five- and six-membered ring lactams have been prepared by first converting an aliphatic alpha,omega-dinitrile to an omega-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax: facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The omega-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate omega-cyanocarboxylic acid or omega-aminocarboxylic acid. Only one of two possible lactam products was produced from alpha-alkyl-substituted alpha,omega-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the omega-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.

  DOI：

  10.1021/jo9804386
• 作为产物：
  描述：

  3-甲基环戊烷-1,2-二胺 在 GA/PEI-cross-linked alginate supported Acidovorax facilis 72W cells 作用下， 以 aq. acetate buffer 为溶剂， 生成 4-cyanopentanoic acid ammonium salt
  参考文献：
  名称：

  Optimization of an Immobilized-Cell Biocatalyst for Production of 4-Cyanopentanoic Acid

  摘要：

  Optimization of microbial cell immobilization, catalyst specific activity, and volumetric productivity were required for scale-up of the nitrilase-catalyzed hydrolysis of 2-methylglutaronitrile to 4-cyanopentanoic acid, an intermediate in the preparation of 1,5-dimethyl-2-piperidone. As an alternative to the immobilization of Acido vorax facilis 72W cells in carrageenan, immobilization in alginate, followed by cross-linking with glutaraldehyde and polyethylenimine, produced a catalyst which was stable in reaction mixtures containing high concentrations of 4-cyanopentanoic acid ammonium salt. Immobilization in alginate produced catalysts with a higher nitrilase specific activity than was achieved in carrageenan, and volumetric productivity of 4-cyanopentanoic acid was increased from 19 to 49 g/L/h. Substituting alginate for carrageenan also eliminated one process step in the immobilization. A further increase in volumetric productivity to 79 g/L/h was achieved by using an immobilized Escherichia coli transformant which expresses A. facilis 72W nitrilase.

  DOI：

  10.1021/op025515k

文献信息

• Isolation and expression of a gene for a nitrilase from Acidovorax facilis 72W
  申请人：——

  公开号：US20030165968A1

  公开（公告）日：2003-09-04

  Recombinant microbial strains are provided that express nitrilase enzyme and are useful as biocatalysts for the hydrolysis of nitrile-containing substrates. The recombinant cells are transformed with a foreign gene isolated from Acidovorax facilis 72W encoding a thermostable nitrilase enzyme that catalyzes the hydrolysis of nitrile-containing substrates to carboxylic acids under mild reaction conditions. The nucleotide sequence of the nitrilase gene and the deduced amino acid sequence encoded by the nitrilase gene are provided.

  提供了表达腈酰化酶的重组微生物菌株，可用作水解含腈底物的生物催化剂。重组细胞转化了从Acidovorax facilis 72W中分离的外源基因，编码一种在温和反应条件下催化腈底物水解生成羧酸的热稳定性腈酰化酶。提供了腈酰化酶基因的核苷酸序列以及腈酰化酶基因编码的推导氨基酸序列。
• ISOLATION AND EXPRESSION OF A GENE FOR A NITRILASE FROM ACIDOVORAX FACILIS 72W
  申请人：——

  公开号：US20040197772A1

  公开（公告）日：2004-10-07

  Recombinant microbial strains are provided that express nitrilase enzyme and are useful as biocatalysts for the hydrolysis of nitrile-containing substrates. The recombinant cells are transformed with a foreign gene isolated from Acidovorax facilis 72W encoding a thermostable nitrilase enzyme that catalyzes the hydrolysis of nitrile-containing substrates to carboxylic acids under mild reaction conditions. The nucleotide sequence of the nitrilase gene and the deduced amino acid sequence encoded by the nitrilase gene are provided.

  提供了表达腈水解酶酶的重组微生物菌株，可用作生物催化剂用于水解含有腈基的底物。重组细胞被转化为从Acidovorax facilis72W中分离的外源基因，编码耐热的腈水解酶酶，在温和反应条件下催化含有腈基的底物水解为羧酸。提供了腈水解酶基因的核苷酸序列和腈水解酶基因编码的推断氨基酸序列。
• Nitrilase-producing acidovorax facilis
  申请人：E. I. du Pont de Nemours & Company

  公开号：US06066490A1

  公开（公告）日：2000-05-23

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α，ω-二腈制备五元环或六元环内酰胺的方法已被开发。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂将脂肪族α，ω-二腈转化为水溶液中的ω-腈酸铵盐。然后，在水溶液中直接将ω-腈酸铵盐转化为相应的内酰胺，而不需要分离中间体ω-腈酸或ω-氨基酸。当脂肪族α，ω-二腈在α-碳原子处也非对称取代时，腈酶以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈酸铵盐，从而在随后的氢化反应中仅产生两种可能的内酰胺产物之一。还提供了一种热处理过程，用于选择理想的区域选择性腈酶或腈水合酶活性并破坏不良活性。
• Preparation of lactams from aliphatic .alpha.,.omega.-dinitriles
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05814508A1

  公开（公告）日：1998-09-29

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrile-carboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α，ω-二腈制备五元环或六元环内酰胺的方法已经开发出来。在该过程中，使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂，首先将脂肪族α，ω-二腈在水溶液中转化为ω-腈基羧酸铵盐。然后，直接在水溶液中将ω-腈基羧酸铵盐转化为相应的内酰胺，而不需要分离中间体ω-腈基羧酸或ω-氨基羧酸。当脂肪族α，ω-二腈在α-碳原子处也被非对称取代时，腈酶以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈基羧酸铵盐，从而在随后的氢化过程中仅产生两种可能的内酰胺产品之一。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。
• Preparation of lactams from aliphatic .alpha..omega.-dinitriles
  申请人：E. I. du Pont de Nemours and Company

  公开号：US06077955A1

  公开（公告）日：2000-06-20

  A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha.,.omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

  一种从脂肪族α,ω-双腈制备五元环或六元环内酰胺的方法已经开发出来。在该过程中，首先使用具有脂肪族腈酶（EC 3.5.5.7）活性或腈水合酶（EC 4.2.1.84）和酰胺酶（EC 3.5.1.4）活性的催化剂将脂肪族α,ω-双腈转化为在水溶液中的ω-腈酸铵盐。然后，将ω-腈酸铵盐直接在水溶液中氢化为相应的内酰胺，而无需分离中间体ω-腈酸或ω-氨基酸。当脂肪族α,ω-双腈在α-碳原子处也不对称取代时，腈酶会以大于98％的区域选择性产生由ω-腈基水解产生的ω-腈酸铵盐，从而在随后的氢化过程中仅产生两种可能的内酰胺产品之一。还提供了一种热处理过程，以选择理想的区域选择性腈酶或腈水合酶活性，同时破坏不良活性。