(2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid

• 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: (2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid
• 英文别名: (2RS,3SR)-2-Acetylamino-3-hydroxy-3-phenyl-propionsaeure；(2S,3R)-2-acetamido-3-hydroxy-3-phenylpropanoic acid
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: KRRUQBRDTUOUGS-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid 在 盐酸 、 硝酸 作用下， 生成 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid
  参考文献：
  名称：

  Woolley, Journal of Biological Chemistry, 1950, vol. 185, p. 293,295

  摘要：

  DOI：
• 作为产物：
  描述：

  (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 在 sodium hydroxide 作用下， 生成 (2RS,3SR)-2-acetylamino-3-hydroxy-3-phenyl-propionic acid
  参考文献：
  名称：

  Some Derivatives of the Stereoisomeric β-Phenylserines. Conversion of the Threo to the Erythro Form

  摘要：

  DOI：

  10.1021/jo50011a022

文献信息

• Biocatalytic Synthesis of Enantiopure β-Methoxy-β-arylalanine Derivatives
  作者：Shiming Fan、Shouxin Liu、Hubo Zhang、Ying Liu、Yihuang Yang、Longyi Jin

  DOI：10.1002/ejoc.201402470

  日期：2014.9

  β-hydroxy-β-arylalanine and β-methoxy-β-arylalanine derivatives, which occur widely in marine nature products, were stereoselectively synthesized with 99 % ee values. The two erythro isomers were prepared by L- or D-aminoacylase-catalyzed resolution of the corresponding N-acetyl derivatives, whereas the two threo isomers were obtained only by D-aminoacylase-catalyzed resolution of the derivatives. erythro-β-Hydroxy-β-arylalanine

  手性β-羟基-β-芳基丙氨酸和β-甲氧基-β-芳基丙氨酸衍生物广泛存在于海洋天然产物中，它们是立体选择性合成的，具有99%的ee值。两种赤型异构体是通过 L-或 D-氨基酰化酶催化拆分相应的 N-乙酰基衍生物制备的，而两种苏型异构体仅通过 D-氨基酰化酶催化拆分衍生物获得。赤型-β-羟基-β-芳基丙氨酸衍生物是通过 2-(羟基亚氨基)-3-氧代-3-芳基丙酸乙酯的非对映选择性氢化制备的，而后者又是通过 3-氧代-3-芳基丙酸乙酯与乙基的肟化而获得的。在纳米 K2CO3 存在下，亚硝酸盐的产率为 72% 至 80%。
• Alberti et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 922,924
  作者：Alberti et al.

  DOI：——

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

  DOI：——

  日期：——
• Hajos, Acta Chimica Academiae Scientiarum Hungaricae, 1959, vol. 21, p. 255,264
  作者：Hajos

  DOI：——

  日期：——
• Peptide inhibitors of CDK2-cyclin A that target the cyclin recruitment-Site: structural variants of the C-Terminal Phe
  作者：Gail E Atkinson、Angela Cowan、Campbell McInnes、Daniella I Zheleva、Peter M Fischer、Weng C Chan

  DOI：10.1016/s0960-894x(02)00508-5

  日期：2002.9

  A focused series of octapeptides based on the lead compound H-His-Ala-Lys-Arg-Arg-Leu-Ile-Phe-NH2 1, in which the C-terminal phenylalanine residue was replaced by alpha and/or beta-modified variants, was synthesized using solid-phase chemistry. Both the L-threo-beta-hydroxy-phenylalanine (beta-phenylserine, Pse) and (2S)-phenylalaninol derivatives, as competitive binders at the cyclin-recruitment site, displayed potent inhibitory activity towards the CDK2-cyclin A complex. Unexpectedly, the D-threo-Pse derivatives also showed inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.