methyl O--(S)-2-hydroxy-3-phenylpropanoate | 131066-56-3

• 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: methyl O--(S)-2-hydroxy-3-phenylpropanoate
• 英文别名: methyl O-(N-carbobenzoxy-L-leucyl)-(S)-2-hydroxy-3-phenylpropanoate；[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl] (2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 131066-56-3
• 化学式: C₂₄H₂₉NO₆
• 分子量: 427.497
• InChiKey: VCSPDTXHDHKENF-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl O--(S)-2-hydroxy-3-phenylpropanoate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 53.0h， 生成 methyl O-<<<(carbobenzoxyamino)methyl>methoxyphosphinyl>-L-leucyl>-(S)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorus-containing inhibitors

  摘要：

  Two series of phosphorus-containing peptide analogues, 3 (Cbz-Gly-psi(PO2-CH2)Leu-Xaa) and 4 (Cbz-Gly-psi-(PO2-NH)Leu-psi[CO2]Xaa), have been synthesized and evaluated as inhibitors of the zinc endopeptidase thermolysin. In comparison with the previously reported phosphonamidates 1, the phosphinates 3 lose only 0.1 kcal/mol in binding affinity, whereas the depsipeptides 4 are bound 2.7 kcal/mol more weakly; these values are contrasted to the 4.0 kcal/mol reduction in binding affinity observed for the phosphonates 2 (Cbz-Gly-psi(PO2-O)Leu-Xaa) in comparison to 1 (Cbz-Gly-psi(PO2-NH)Leu-Xaa). The observed effects are interpreted through consideration of the differences in active-site and solvent interactions. For the comparison between the diamides 1 and the depsipeptides 4, a full accounting of the balance between these interactions can be approached. The arylphosphonates 5 (Aryl-psi(PO2-O)Leu-Leu) were synthesized and evaluated to investigate the importance of phosphonate basicity on the overall binding affinity of these zinc-coordinating inhibitors; the inhibitor K(i) values were found to be independent of phosphonate p(K)a, indicating that the basicity of the phosphonate moiety exerts counterbalancing effects on the energies of zinc coordination and solvation. For analysis of the influence of structural variations on observed affinity, the definition of "differential binding energy" is introduced as a practical alternative to the concept of "intrinsic binding energy".

  DOI：

  10.1021/ja00001a043
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 、 L-苯基乳酸甲酯 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到methyl O--(S)-2-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Differential binding energy: a detailed evaluation of the influence of hydrogen-bonding and hydrophobic groups on the inhibition of thermolysin by phosphorus-containing inhibitors

  摘要：

  Two series of phosphorus-containing peptide analogues, 3 (Cbz-Gly-psi(PO2-CH2)Leu-Xaa) and 4 (Cbz-Gly-psi-(PO2-NH)Leu-psi[CO2]Xaa), have been synthesized and evaluated as inhibitors of the zinc endopeptidase thermolysin. In comparison with the previously reported phosphonamidates 1, the phosphinates 3 lose only 0.1 kcal/mol in binding affinity, whereas the depsipeptides 4 are bound 2.7 kcal/mol more weakly; these values are contrasted to the 4.0 kcal/mol reduction in binding affinity observed for the phosphonates 2 (Cbz-Gly-psi(PO2-O)Leu-Xaa) in comparison to 1 (Cbz-Gly-psi(PO2-NH)Leu-Xaa). The observed effects are interpreted through consideration of the differences in active-site and solvent interactions. For the comparison between the diamides 1 and the depsipeptides 4, a full accounting of the balance between these interactions can be approached. The arylphosphonates 5 (Aryl-psi(PO2-O)Leu-Leu) were synthesized and evaluated to investigate the importance of phosphonate basicity on the overall binding affinity of these zinc-coordinating inhibitors; the inhibitor K(i) values were found to be independent of phosphonate p(K)a, indicating that the basicity of the phosphonate moiety exerts counterbalancing effects on the energies of zinc coordination and solvation. For analysis of the influence of structural variations on observed affinity, the definition of "differential binding energy" is introduced as a practical alternative to the concept of "intrinsic binding energy".

  DOI：

  10.1021/ja00001a043

文献信息

• DIDEPSIPEPTIDE-BASED ENDOPARASITICIDES, NEW DIDEPSIPEPTIDES AND PROCESS FOR PREPARING THE SAME
  申请人：——

  公开号：US20020142969A1

  公开（公告）日：2002-10-03

  The present invention relates to the use of didepsipepides of the general formula (I) and their salts 1 in which the radicals have the meaning given in the description, and to new didepsidpeptides and processes for their preparation.

  本发明涉及使用一般式(I)的二脱氨肽和其盐，其中基团的含义如描述所示，并涉及新的二脱氨肽和其制备方法。
• Didepsipeptide-based endoparasiticides, new didepsipeptides and process for preparing the same
  申请人：——

  公开号：US20040034048A1

  公开（公告）日：2004-02-19

  The present invention relates to the use of didepsipeptides of the general formula (I) and their salts 1 in which the radicals have the meaning given in the description, and to new didepsidpeptides and processes for their preparation.

  本发明涉及使用通式（I）的二肽酯及其盐，其中基团的含义如描述中所述，以及新的二肽酯和其制备方法。
• ENDOPARASITIZIDE MITTEL AUF BASIS VON DIDEPSIPEPTIDEN, NEUE DIDEPSIPEPTIDE UND VERFAHREN ZU IHRER HERSTELLUNG
  申请人：BAYER AG

  公开号：EP0843658B1

  公开（公告）日：2002-12-18
• US6110928A
  申请人：——

  公开号：US6110928A

  公开（公告）日：2000-08-29
• US6291472B1
  申请人：——

  公开号：US6291472B1

  公开（公告）日：2001-09-18