(E)-(S)-4-Amino-5-phenyl-pent-2-enoic acid | 267008-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(S)-4-Amino-5-phenyl-pent-2-enoic acid
• 英文别名: (2E)-4-Amino-5-phenyl-2-pentenoic acid；(E,4S)-4-amino-5-phenylpent-2-enoic acid
• CAS: 267008-78-6
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: BIRNUNMJYUTJQL-VQCYPWCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-Amino-5-phenyl-pent-2-enoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (E,4S)-N-[2-(ethylamino)ethyl]-5-phenyl-4-[(4-phenylphenyl)carbamoylamino]pent-2-enamide
  参考文献：
  名称：

  Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives

  摘要：

  Several beta- and gamma-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipophilic side chains were tolerated in the beta-amino acid series (i.e., Ph, CH2Ph, CH(CH3)(2), and CH2CH(CH3)(2)). In the gamma-amino acid series, minimal differences in potency were observed between the alpha, beta-unsaturated analogs and the corresponding saturated derivatives. In both series, a 4-biphenyl or 4-phenoxyphenyl substituent appended to the urea or cyanogunaidine moiety was necessary for in vitro activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.043
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-(S)-4-Amino-5-phenyl-pent-2-enoic acid
  参考文献：
  名称：

  单晶中设计的三链[小β]片的结构特征和分子聚集

  摘要：

  报道了由E-葡萄酒残基组成的杂合三链β-小薄片的设计，合成和单晶构象。通过在表面处插入碳-碳双键来限制小β链的构象柔韧性。

  DOI：

  10.1039/c6cc00127k

文献信息

• Self-Assembly to Function: Design, Synthesis, and Broad Spectrum Antimicrobial Properties of Short Hybrid <i>E</i>-Vinylogous Lipopeptides
  作者：S. Shiva Shankar、Sushil N. Benke、Narem Nagendra、Prabhakar Lal Srivastava、Hirekodathakallu V. Thulasiram、Hosahudya N. Gopi

  DOI：10.1021/jm400884w

  日期：2013.11.14

  Nonribosomal E-vinylogous gamma-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating alpha-and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the alpha-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.
• Structural features and molecular aggregations of designed triple-stranded β-sheets in single crystals
  作者：Anupam Bandyopadhyay、Rajkumar Misra、Hosahudya N. Gopi

  DOI：10.1039/c6cc00127k

  日期：——

  Design, synthesis and single crystal conformations of hybrid triple-stranded [small beta]-sheets composed of E-vinylogous residues are reported. Restricting conformational flexibility of [small beta]-strands through the insertion of carbon-carbon double bonds at facing...

  报道了由E-葡萄酒残基组成的杂合三链β-小薄片的设计，合成和单晶构象。通过在表面处插入碳-碳双键来限制小β链的构象柔韧性。
• Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives
  作者：Ronald L Wolin、Alejandro Santillán、Tristin Barclay、Liu Tang、Hariharan Venkatesan、Sandy Wilson、Doo Hyun Lee、Timothy W Lovenberg

  DOI：10.1016/j.bmc.2004.05.043

  日期：2004.8

  Several beta- and gamma-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipophilic side chains were tolerated in the beta-amino acid series (i.e., Ph, CH2Ph, CH(CH3)(2), and CH2CH(CH3)(2)). In the gamma-amino acid series, minimal differences in potency were observed between the alpha, beta-unsaturated analogs and the corresponding saturated derivatives. In both series, a 4-biphenyl or 4-phenoxyphenyl substituent appended to the urea or cyanogunaidine moiety was necessary for in vitro activity. (C) 2004 Elsevier Ltd. All rights reserved.