(2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid | 135457-26-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid
• CAS: 135457-26-0
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: WQLIGWIJZBHBFM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-犬尿氨酸 、 苯甲醛 在 kynureninase from Pseudomonas fluorescens (ATTC 11250) 、 磷酸吡哆醛 作用下， 反应 8.0h， 生成 (2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid 、 (2S,4S)-2-amino-4-hydroxy-4-phenylbutanoic acid
  参考文献：
  名称：

  Kynureninase in Organic Synthesis: Preparation of γ-Hydroxy-α-l-Amino Acids

  摘要：

  已知喹啉酶可催化苯甲醛和喹啉之间的转醛反应，它接受多种其他芳香醛和丙炔醛作为底物，生成新型的γ-羟基-α-氨基酸。使用d-和l-氨基酸氧化酶的酶促方法证实了α-碳的l-构型。通过在γ-羟基-α-氨基酸衍生的内酯的核磁共振光谱中观察到的NOE，确定主要异构体中新形成的手性中心（γ位）的立体化学结构为R构型。

  DOI：

  10.1055/s-1998-3137

文献信息

• Stereochemistry and mechanism of aldol reactions catalyzed by kynureninase
  作者：Robert S. Phillips、Rajesh K. Dua

  DOI：10.1021/ja00019a039

  日期：1991.9

  Kynureninase from Pseudomonas has been reported to catalyze aldol and retro-aldol reactions, in addition to the physiological hydrolytic cleavage of L-kynurenine to anthranilic acid and L-alanine. However, the stereochemistry of these novel aldol reactions has not been previously determined. We have determined that the reaction of L-kynurenine and benzaldehyde catalyzed by kynureninase results in (2S,4R)-2-amino-4-hydroxy-4-phenylbutanoic acid. Similarly, the 4R isomer of dihydro-L-kynurenine readily undergoes retro-aldol cleavage, while the 4S isomer is unreactive as a substrate. Both isomers of dihydro-L-kynurenine are competitive inhibitors of kynureninase from Pseudomonas. However, the 4S isomer of dihydro-L-kynurenine is the most potent inhibitor, with a K(i) of 0.3-mu-M. These results provide additional support for a general base mechanism for kynureninase, and suggest that the hydration occurs on the re face of the carbonyl group of kynurenine to give an (S)-gem-diolate intermediate.
• INHIBITORS OF KYNURENINASE
  申请人：THE UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：EP0581907A1

  公开（公告）日：1994-02-09
• US5254725A
  申请人：——

  公开号：US5254725A

  公开（公告）日：1993-10-19
• US5442104A
  申请人：——

  公开号：US5442104A

  公开（公告）日：1995-08-15
• US5516936A
  申请人：——

  公开号：US5516936A

  公开（公告）日：1996-05-14