4-cyano-3-hydroxybutyric acid | 147028-51-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 4-cyano-3-hydroxybutyric acid
• 英文别名: 3-hydroxybutyric acid；3-hydroxy-4-cyano-butyric acid；4-cyano-3-hydroxybutanoic acid；β-Oxy-γ-cyan-buttersaeure；β-Oxy-glutarsaeure-mononitril；4-Cyan-3-hydroxy-buttersaeure；4-cyano-3-hydroxybutanoate
• CAS: 147028-51-1
• 化学式: C₅H₇NO₃
• mdl: MFCD19228517
• 分子量: 129.115
• InChiKey: ADZQCEUEGXRCJY-UHFFFAOYSA-N

物化性质

• 沸点：
  420.5±35.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 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：
  81.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-3-hydroxybutyric acid 在 platinum(IV) oxide 氯化亚砜 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 生成 4-羟基-2-哌啶酮
  参考文献：
  名称：

  A Stereodivergent Approach to Substituted 4-Hydroxypiperidines

  摘要：

  A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation.

  DOI：

  10.1021/jo025943o
• 作为产物：
  描述：

  ethyl 4-cyano-3-hydroxybutanoate 在 氢氧化钾 作用下， 生成 4-cyano-3-hydroxybutyric acid
  参考文献：
  名称：

  Lespieau, Bulletin de la Societe Chimique de France, 1923, vol. <4>33, p. 731,732

  摘要：

  DOI：

文献信息

• Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications
  作者：Avinash Vellore Sunder、Shikha Shah、Pratima Rayavarapu、Pramod P. Wangikar

  DOI：10.1016/j.procbio.2020.05.004

  日期：2020.7

  identified nine novel nitrilase sequences from bacteria and evaluated their activity on a broad spectrum of 23 industrially relevant nitrile substrates. Nitrilases from Zobellia galactanivorans, Achromobacter insolitus and Cupriavidus necator were highly active on varying classes of nitriles and applied as whole cell biocatalysts in lab scale processes. Z. galactanivorans nitrilase could convert 4-cyanopyridine

  摘要 腈水解酶将腈酶促转化为羧酸在多种药物前体和精细化学品的绿色合成中具有重要意义。尽管已经对来自多种来源的腈水解酶进行了表征，但仍存在确定表现出更高底物耐受性和更好热稳定性的广谱腈水解酶以开发工业相关生物催化过程的范围。通过基因组挖掘，我们从细菌中鉴定了 9 种新型腈水解酶序列，并评估了它们对 23 种工业相关腈底物的广谱活性。来自 Zobellia galactanivorans、Achromobacter insolitus 和 Cupriavidus necator 的腈水解酶对不同种类的腈具有高度活性，并在实验室规模的过程中用作全细胞生物催化剂。Z。galactanivorans 腈水解酶可以通过补料分批添加底物在 3 小时内转化 4-氰基吡啶以达到 1.79 M 异烟酸的产量。来自 A. insolitus 的腈水解酶可以快速水解 630 mM 亚氨基二乙腈，在 1 小时内将 86%
• Selective Hydrolysis of Aliphatic Dinitriles to Monocarboxylic Acids by a Nitrilase from Arabidopsis thaliana
  作者：Franz Effenberger、Steffen Oßwald

  DOI：10.1055/s-2001-17523

  日期：——

  The hydrolysis of a variety of dinitriles including α,ω-dicyanoalkanes 1, β-substituted glutaronitriles 5, and γ-cyanopimelonitrile 7 with a recombinant plant nitrilase from Arabidopsis thaliana, expressed in E. coli, is described. Conversion rate and selectivity of the hydrolysis of dinitriles 1a-f to ω-cyanocarboxylic acids 2a-f depend on the chain length. The enzyme activity markedly increases from malononitrile (1a) to octanedinitrile (1f). The selectivity, however, does not correlate with the rates. Up to a chain length of 6 C-atoms, the cyanocarboxylic acid is the only product, even at complete conversion of the starting material. Pimelonitrile (1e) is hydrolyzed to the cyanocarboxylic acid 2e without formation of diacid (<1%) up to 73% conversion. Glutaronitriles 5a-c were also hydrolyzed to the corresponding cyanobutanoic acids 6a-c with perfect selectivity. The nitrilase hydrolyzes exclusively the primary cyano group of 7 to give 3,5-dicyanoheptanoic acid (8a), whereby the selectivity is slightly reduced compared to the unsubstituted pimelonitrile (1e). If the hydrolysis is terminated at conversions ≤90%, pure 8a can be isolated in 72% yield (92% referred to conversion). After esterification of 8a to the methyl ester 8b, only the 5-cyano group but not the ester function was hydrolyzed enzymatically to give cyanoheptanedioic acid monoester (10).

  描述了使用来自阿拉伯芥（Arabidopsis thaliana）的重组植物腈水解酶在大肠杆菌中表达，对多种二腈（dinitriles）进行水解的过程，这些二腈包括α,ω-二氰烷烃1、β-取代的戊二腈5和γ-氰基庚腈7。二腈1a-f转化为ω-氰基羧酸2a-f的水解转化率和选择性依赖于链长。从丙二腈（1a）到辛烯二腈（1f），酶活性显著增加。然而，选择性与转化速率并不相关。对于6个碳原子以下的链长，氰基羧酸是唯一的产品，即使起始材料完全转化。庚腈（1e）在转化率达到73%时，仅被水解为氰基羧酸2e，而未形成二酸（<1%）。戊二腈5a-c也被水解为相应的氰基丁酸6a-c，具有完美的选择性。腈水解酶专门水解7的原料氰基，生成3,5-二氰基庚酸（8a），相比于未取代的庚腈（1e），选择性略有降低。如果在转化率≤90%时终止水解，可以以72%的产率（转化率92%）单独分离出纯8a。在将8a酯化为甲酯8b后，只有5-氰基基团而不是酯功能被酶催化水解，生成氰基庚二酸单酯（10）。
• Process for producing optically active 4-halo-3-hydroxybutanoate
  申请人：——

  公开号：US20030134402A1

  公开（公告）日：2003-07-17

  There are provided a polynucleotide sequence coding for an amino acid sequence capable of preferentially producing (S)-4-bromo-3-hydroxy-butanoate by asymmetrically reducing 4-bromo-3-oxobutanoate, A DNA construct having a promoter in operative linkage with the polynucleotide sequence, a recombinant vector containing the polynucleotide sequences a transformant, a recombinant vector and the like.

  提供了一个编码氨基酸序列的多核苷酸序列，能够通过不对称还原4-溴-3-氧代丁酸而优先产生（S）-4-溴-3-羟基丁酸，具有启动子与多核苷酸序列在操作连接的DNA构建物，含有多核苷酸序列的重组载体，一种转化体，一种重组载体等。
• Process for producing optically active-4-halo-3-hydroxybutanoate
  申请人：Asako Hiroyuki

  公开号：US20050019816A1

  公开（公告）日：2005-01-27

  There are provided a polynucleotide sequence coding for an amino acid sequence capable of preferentially producing (S)-4-bromo-3-hydroxybutanoate by asymmetrically reducing 4-bromo-3-oxobutanoate, A DNA construct having a promoter in operative linkage with the polynucleotide sequence, a recombinant vector containing the polynucleotide sequence, a transformant, a recombinant vector and the like.

  提供了一个多核苷酸序列，编码一个能够优先产生(S)-4-溴-3-羟基丁酸的氨基酸序列，通过将4-溴-3-氧代丁酸不对称还原。该多核苷酸序列与启动子构成操作性连接的DNA构建物，重组载体含有该多核苷酸序列，转化体，重组载体等。
• [EN] PROCESSES FOR MAKING (R)-ETHYL 4-CYANO-3-HYDROXYBUTYRIC ACID<br/>[FR] PROCEDES DE PRODUCTION D'ACIDE (R)-ETHYL 4-CYANO-3-HYDROXYBUTYRIQUE
  申请人：——

  公开号：WO2003106415A3

  公开（公告）日：2004-07-01

表征谱图