L-β-4-bromophenylserine

• 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: L-β-4-bromophenylserine
• 英文别名: (2S)-2-amino-3-(4-bromophenyl)-3-hydroxypropanoic acid
• 化学式: C₉H₁₀BrNO₃
• 分子量: 260.087
• InChiKey: KCLZGAAUWWGOBN-JAMMHHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  对溴苯甲醛 、 聚甘氨酸 在 potassium dihydrogenphosphate 、 Pseudomonas putida L-threonine aldolase 、 磷酸吡哆醛 作用下， 反应 1.0h， 以47%的产率得到L-β-4-bromophenylserine
  参考文献：
  名称：

  Threonine aldolases—an emerging tool for organic synthesis

  摘要：

  In a systematic study, 21 ring-substituted benzaldehydes were reacted with glycine under catalysis with a L-threonine aldolase (LTA) from Pseudomonas putida and a D-threonine aldolase (DTA) from Alcaligenes xylosoxidans to form the corresponding beta-hydroxy-alpha-amino acids 1-18. DTA proved to be highly selective with ee's > 99% (D) and de's up to 99% (syn). Two thiamphenicol precursors were synthesized utilizing DTA on a preparative scale. LTA-catalyzed reactions led to ee's > 99% (L) but low to moderate de's (20-50%, syn). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.035

文献信息

• Threonine aldolases—an emerging tool for organic synthesis
  作者：Johannes Steinreiber、Kateryna Fesko、Christoph Reisinger、Martin Schürmann、Friso van Assema、Michael Wolberg、Daniel Mink、Herfried Griengl

  DOI：10.1016/j.tet.2006.11.035

  日期：2007.1

  In a systematic study, 21 ring-substituted benzaldehydes were reacted with glycine under catalysis with a L-threonine aldolase (LTA) from Pseudomonas putida and a D-threonine aldolase (DTA) from Alcaligenes xylosoxidans to form the corresponding beta-hydroxy-alpha-amino acids 1-18. DTA proved to be highly selective with ee's > 99% (D) and de's up to 99% (syn). Two thiamphenicol precursors were synthesized utilizing DTA on a preparative scale. LTA-catalyzed reactions led to ee's > 99% (L) but low to moderate de's (20-50%, syn). (c) 2006 Elsevier Ltd. All rights reserved.