(S)-3-cinnamamido-3-phenylpropanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-3-cinnamamido-3-phenylpropanoic acid
• 英文别名: (S)-3-Phenyl-3-[(E)-(3-phenyl-acryloyl)amino]-propionic acid；(3S)-3-phenyl-3-[[(E)-3-phenylprop-2-enoyl]amino]propanoic acid
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: HRFSFMGGKARXEO-PCUGXKRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-3-cinnamamido-3-phenylpropanoic acid 、 (3S)-L-valine-(4S)-methylsuccinimide 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S)-N-[(2S)-3-methyl-1-[(3R,4S)-4-methyl-2,5-dioxopyrrolidin-3-yl]-1-oxobutan-2-yl]-3-phenyl-3-[[(E)-3-phenylprop-2-enoyl]amino]propanamide
  参考文献：
  名称：

  Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action

  摘要：

  The pseudopeptide pyrrolidinedione natural products moiramide B and andrimid represent a new class of antibiotics that target bacterial fatty acid biosynthesis. Structure activity relationship (SAR) studies revealed a high degree of variability for the fatty acid side chain, allowing optimization of physicochemical parameters, and a restricted SAR for the pyrrolidinedione group, indicating major relevance of this subunit for efficient target binding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.002
• 作为产物：
  描述：

  (betaS)-beta-氨基苯丙酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-cinnamamido-3-phenylpropanoic acid
  参考文献：
  名称：

  山梨酸尾部对 Moiramide B 抗菌和抗结核特性作用的再研究

  摘要：

  新子口袋：在这项研究中，我们证明了假肽 moiramide B 的山梨酸尾部对于乙酰辅酶 A 羧化酶结合是必不可少的。基于结构-活性和分子建模数据，为 N-末端修饰的莫拉酰胺衍生物开发了结合模型。

  DOI：

  10.1002/cmdc.202200631

文献信息

• Insights into the Mechanistic Pathway of the<i>Pantoea agglomerans</i>Phenylalanine Aminomutase
  作者：Susan Strom、Udayanga Wanninayake、Nishanka Dilini Ratnayake、Kevin D. Walker、James H. Geiger

  DOI：10.1002/anie.201108525

  日期：2012.3.19

  The structure of the title aminomutase has been solved. The steric bulk of Phe 455 (green CPK structure) twists the phenylpropanoate ligand (green stick) by approximately 15° about the Cβ axis, which precludes a stronger bidentate salt bridge with Arg 323 (magenta structure). Instead, a weaker monodentate bridge may partially explain the different configuration of the product, relative to that obtained

  标题氨基变位酶的结构已解决。Phe 455（绿色CPK结构）的空间体积使苯基丙酸酯配体（绿色棒）绕Cβ轴扭曲了大约15° ，这排除了具有Arg 323（品红色结构）的更强的双齿盐桥。相反，相对于用形成双齿中间体的同工酶所获得的构型，较弱的单齿桥可以部分解释产物的不同构型。
• Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action
  作者：Jens Pohlmann、Thomas Lampe、Mitsuyuki Shimada、Peter G. Nell、Josef Pernerstorfer、Niels Svenstrup、Nina A. Brunner、Guido Schiffer、Christoph Freiberg

  DOI：10.1016/j.bmcl.2004.12.002

  日期：2005.2

  The pseudopeptide pyrrolidinedione natural products moiramide B and andrimid represent a new class of antibiotics that target bacterial fatty acid biosynthesis. Structure activity relationship (SAR) studies revealed a high degree of variability for the fatty acid side chain, allowing optimization of physicochemical parameters, and a restricted SAR for the pyrrolidinedione group, indicating major relevance of this subunit for efficient target binding. (C) 2004 Elsevier Ltd. All rights reserved.
• A Reinvestigation of the Role of the Sorbic Acid Tail on the Antibacterial and Anti‐Tuberculosis Properties of Moiramide B
  作者：Irina Kollmorgen、Nathalie Bachmann、Michael Dal Molin、Carsten Degenhart、Eldar Zent、Vikram Pareek、Uwe Koch、Jan Rybniker、Nils Metzler-Nolte、Raphael Stoll、Bert Klebl、Julia Elisabeth Bandow、Jürgen Scherkenbeck

  DOI：10.1002/cmdc.202200631

  日期：——

  New subpocket: In this study we demonstrate that the sorbic acid tail of the pseudopeptide moiramide B is essential for acetyl-CoA carboxylase binding. Based on structure–activity and molecular modeling data, a binding model was developed for N-terminally modified moiramide derivatives.

  新子口袋：在这项研究中，我们证明了假肽 moiramide B 的山梨酸尾部对于乙酰辅酶 A 羧化酶结合是必不可少的。基于结构-活性和分子建模数据，为 N-末端修饰的莫拉酰胺衍生物开发了结合模型。