(E)-(S)-2-Hydroxy-4-(2-nitro-phenyl)-but-3-enoic acid | 192204-21-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-(S)-2-Hydroxy-4-(2-nitro-phenyl)-but-3-enoic acid
• 英文别名: (E,2S)-2-hydroxy-4-(2-nitrophenyl)but-3-enoic acid
• CAS: 192204-21-0
• 化学式: C₁₀H₉NO₅
• 分子量: 223.185
• InChiKey: WCADJIXQCONAID-CYNONHLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(S)-2-Hydroxy-4-(2-nitro-phenyl)-but-3-enoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 15.0h， 生成 (S)-4-(2-Amino-phenyl)-2-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p
• 作为产物：
  描述：

  Sodium; (E)-4-(2-nitro-phenyl)-2-oxo-but-3-enoate 在 盐酸 、 1,4-dihydronicotinamide adenine dinucleotide 、 sodium formate 、 三羟甲基氨基甲烷盐酸盐 、 1,4-二巯基-2,3-丁二醇 作用下， 以 水 为溶剂， 反应 24.0h， 以98%的产率得到(E)-(S)-2-Hydroxy-4-(2-nitro-phenyl)-but-3-enoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of a Thymine Derivative of (S)-2-Hydroxy-4-(2-aminophenyl)butanoic Acid. A Novel Building Block for the Synthesis of Aromatic Peptidic Nucleic Acid Oligomers¹

  摘要：

  The synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical peptide synthesis. UV absorption spectra and H-1 NMR data of this tetramer suggested that base stacking interactions in the APNA oligomers may be favorable.

  DOI：

  10.1021/jo962326p

文献信息

• Expanding Synthetic Applications of Δ¹‐Piperidine‐2‐carboxylate/Δ¹‐pyrroline‐2‐carboxylate Reductase from <i>Pseudomonas syringae</i> (DpkA_{<i>Psyrin</i>}). Biocatalytic Asymmetric Synthesis of (<i>S</i>,<i>E</i>)‐2‐hydroxy‐4‐arylbut‐3‐enoic Acid Derivatives
  作者：Carlos J. Moreno、Samantha Gittings、Dieter Schollmeyer、Jesús Joglar、Jordi Bujons、Karel Hernández、Pere Clapés

  DOI：10.1002/adsc.202300953

  日期：2024.2.20

  this side reaction competes with 3 a for the NADPH regeneration lowering the yield. In addition, equilibrium limitations of the aldol condensation reaction can also affect the final yield of 4 a, when both HBPAPputida and DpkAPsyrin, are present in the reaction mixture. Thus, the successful cascade process will depend on both the efficiency of the aldol condensation (i. e., kinetics and reaction equilibrium)

  手性2-羟基-4-芳基丁-3-烯酸衍生物是合成血管紧张素转换酶(ACE)抑制剂的重要前体，例如依那普利、赖诺普利、西拉普利或贝那普利。在这项工作中，我们利用来自丁香假单胞菌的 Δ 1 -哌​​啶-2-羧酸盐/Δ 1 -吡咯啉-2-羧酸盐还原酶的未探索的混杂酮还原酶活性。番茄 DSM 50315 (DpkA Psyrin ) 用于合成 ( S , E )-2-羟基-4-芳基丁-3-烯酸。该策略被设计为酶级联，包括丙酮酸与芳基醛之间的羟醛缩合，由反式催化来自恶臭假单胞菌(HBPA Pputida )的 -o-羟基亚苄基丙酮酸水合酶-醛缩酶，用于构建碳支架，以及随后由 DpkA Psyrin催化的羰基的不对称还原。酶级联提供了定量转化，总体分离产量在 57-85% 之间。总共制备了九种结构不同的 ( S , E )-2-羟基-4-芳基丁-3-烯酸，ee 含量在 87-99% 之间。