L-4-fluorothreonine

• 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-4-fluorothreonine
• 英文别名: (2S)-2-amino-4-fluoro-3-hydroxybutanoic acid
• 化学式: C₄H₈FNO₃
• 分子量: 137.111
• InChiKey: GTFWIYJIEXNAOL-NFJMKROFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氟乙醛 、 聚甘氨酸 在 glycine hydroxymethyltransferase 磷酸吡哆醛 作用下， 以 phosphate buffer 为溶剂， 反应 3.0h， 以50%的产率得到L-4-fluorothreonine
  参考文献：
  名称：

  Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases

  摘要：

  The L-and D-threonine aldolase catalyzed formation of gamma-halogenated and long-chain L-and D-3-alkylserine-derivatives 1-12, respectively, was shown starting from glycine and halogenated C-2-or C-4-C-12 aldehydes. LTA from Pseudomonas putida accepted all tested aldehydes with strongly varying diastereoselectivity (de up to 93%). Only aldehydes smaller than decanal were converted by DTA from Alcaligenes xylosoxidans with good selectivities (de up to 73%). Utilizing isobutanal enantio-and diastereopure D-syn-2-amino-3-hydroxy-4-methylpentanoic acid was obtained (ee> 99%, de> 95%), which was converted to the corresponding 2-amino-1,3-diol. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.013

文献信息

• Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1,3-diols using threonine aldolases
  作者：Johannes Steinreiber、Kateryna Fesko、Clemens Mayer、Christoph Reisinger、Martin Schürmann、Herfried Griengl

  DOI：10.1016/j.tet.2007.06.013

  日期：2007.8

  The L-and D-threonine aldolase catalyzed formation of gamma-halogenated and long-chain L-and D-3-alkylserine-derivatives 1-12, respectively, was shown starting from glycine and halogenated C-2-or C-4-C-12 aldehydes. LTA from Pseudomonas putida accepted all tested aldehydes with strongly varying diastereoselectivity (de up to 93%). Only aldehydes smaller than decanal were converted by DTA from Alcaligenes xylosoxidans with good selectivities (de up to 73%). Utilizing isobutanal enantio-and diastereopure D-syn-2-amino-3-hydroxy-4-methylpentanoic acid was obtained (ee> 99%, de> 95%), which was converted to the corresponding 2-amino-1,3-diol. (c) 2007 Elsevier Ltd. All rights reserved.