2-carboxymethoxy-D-phenylalanine | 1336479-77-6

• 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: 2-carboxymethoxy-D-phenylalanine
• 英文别名: (2R)-2-amino-3-[2-(carboxymethoxy)phenyl]propanoic acid
• CAS: 1336479-77-6
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: KSJSIZOKPWUWAD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲酰基苯氧基醋酸乙酯 在 palladium on activated charcoal 、 vigna angularis D-hydantoinase 、 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 158.0h， 生成 2-carboxymethoxy-D-phenylalanine
  参考文献：
  名称：

  Biotransformation of new racemic (R,S)-5-benzylhydantoin derivatives by D-hydantoinases from adzuki bean

  摘要：

  In the present work the scope of D-hydantoinase enzyme application was increased towards new racemic (R, S) -5-benzylhydantoin derivatives. Five new substrates for the D-hydantoinase (R,S)-5-(3'-carboxybenzyl) hydantoin, (R, S)-5-(4'carboxybenzyl) hydantoin, (R,S)-5-(2'-carbomethoxybenzyl) hydantoin, (R,S)-5-(3'-carbomethoxybenzyl) hydantoin and (R,S)-5-(4'(4-ethoxycarboxy) propoxybenzyl) hydantoin were synthesised and converted using a two-step hydantoinase process into their corresponding D-phenylalanine derivatives. In this study two D-hydantoinases from Vigna angularis (adzuki bean) obtained from commercial sources were used: pure, isolated directly from Vigna angularis (V.a.D-HYD) 494 U/g and immobilised, recombinant, cloned and expressed in Escherichia coli (rD-HYD) 53.1 U/g. The results obtained showed that the examined enzymes catalysed hydrolysis of all new substrates into their corresponding N-carbamoyl-D-phenylalanine derivatives. High enantiomeric purities of the resulting D-phenylalanine derivatives were also determined. However, very low conversion yields of (R,S)-5-(3'-carboxybenzyl) hydantoin and (R, S)-5-(2'-carbomethoxybenzyl) hydantoin to corresponding N-carbamoyl-D amino acid were observed. Three D-phenylalanine derivatives: 4-carboxy-D-phenylalanine, 3-carbomethoxy-D-phenylalanine and 4-carbopropoxy-D-phenylalanine were obtained and isolated from the reaction mixtures using ion-exchange chromatography.

  DOI：

  10.3109/10242422.2014.893578