(threo)-3-(4-hydroxyphenyl)serine | 6809-69-4

• 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: (threo)-3-(4-hydroxyphenyl)serine
• 英文别名: (+/-)-threo-<4-Hydroxy-phenyl>-serin；(2RS.3SR)-2-amino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid；(2RS.3SR)-2-Amino-3-hydroxy-3-(4-hydroxy-phenyl)-propionsaeure；(R)-3-hydroxy-L-tyrosine；(2S,3R)-2-azaniumyl-3-hydroxy-3-(4-hydroxyphenyl)propanoate
• CAS: 6809-69-4；17580-59-5；19866-23-0；19866-24-1；37925-20-5；74365-43-8；147331-52-0；147331-53-1
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: RKCRKDKQUDBXAU-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 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：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (threo)-3-(4-hydroxyphenyl)serine 生成 (2R,3S)-(D-threo)-3-(4-hydroxyphenyl)serine
  参考文献：
  名称：

  Herbert, Richard B.; Wilkinson, Barrie; Ellames, George J., Canadian Journal of Chemistry, 1994, vol. 72, # 1, p. 114 - 117

  摘要：

  DOI：
• 作为产物：
  描述：

  N-<4-Hydroxy-benzyliden>-glycin 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (threo)-3-(4-hydroxyphenyl)serine
  参考文献：
  名称：

  Herbert, Richard B.; Wilkinson, Barrie; Ellames, George J., Canadian Journal of Chemistry, 1994, vol. 72, # 1, p. 114 - 117

  摘要：

  DOI：

文献信息

• Ehrhart; Hennig, Chemische Berichte, 1954, vol. 87, p. 892,899
  作者：Ehrhart、Hennig

  DOI：——

  日期：——
• Holland et al., Journal of the Chemical Society, 1953, p. 273,276
  作者：Holland et al.

  DOI：——

  日期：——
• The Preparation of Hydroxyphenylserines from Benzyloxybenzaldehydes and Glycine¹
  作者：William A. Bolhofer

  DOI：10.1021/ja01634a039

  日期：1954.3
• 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.
• ENGINEERED ALDOLASE POLYPEPTIDES AND USES THEREOF
  申请人：Enzymaster (Ningbo) Bio-Engineering Co., Ltd

  公开号：US20200123525A1

  公开（公告）日：2020-04-23

  The present invention provides engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The present disclosure also provides polynucleotides encoding engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides of the present invention for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. So, it has good industrial application prospects.