(2S)-2-aminoheptadecanoic acid | 1254251-29-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-2-aminoheptadecanoic acid
• CAS: 1254251-29-0
• 化学式: C₁₇H₃₅NO₂
• 分子量: 285.47
• InChiKey: CRJWOABTAHMMSA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (2S)-2-aminoheptadecanoic acid 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以11.4 mg的产率得到L-Ala-NH2-DNP-L-pentadecylglycine
  参考文献：
  名称：

  Mechanistic Analysis of Muraymycin Analogues: A Guide to the Design of MraY Inhibitors

  摘要：

  The systematic structure activity relationship (SAX) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAX of the accessory urea peptide moiety indicated that it could be simplified. Our SAX study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop S. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs.

  DOI：

  10.1021/jm200906r
• 作为产物：
  描述：

  1-十四烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 barium hydroxide octahydrate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 30.33h， 生成 (2S)-2-aminoheptadecanoic acid
  参考文献：
  名称：

  Mechanistic Analysis of Muraymycin Analogues: A Guide to the Design of MraY Inhibitors

  摘要：

  The systematic structure activity relationship (SAX) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAX of the accessory urea peptide moiety indicated that it could be simplified. Our SAX study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop S. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs.

  DOI：

  10.1021/jm200906r

文献信息

• Separation medium
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0300448A2

  公开（公告）日：1989-01-25

  A separation medium useful as an adsorbent of liquid chromatography for optical resolution of racemic mixtures is disclosed, which comprises a reversed phase support coated with an optically active amino acid derivative represented by formula (I): wherein R₁ represents a straight or branched alkyl group having from 1 to 3 carbon atoms; and R₂ and R₃ each represents a straight or branched alkyl group having from 4 to 12 carbon atoms which may contain an aromatic group or an unsaturated alkyl group. The separation medium is applicable to optical resolution of a wide range of DL-amino acids and exhibits excellent durability.

  本发明公开了一种可用作液相色谱吸附剂的分离介质，用于外消旋混合物的光学分 解，该分离介质包括涂有由式(I)表示的光学活性氨基酸衍生物的反相支持物： 其中 R₁ 代表具有 1 至 3 个碳原子的直链或支链烷基；R₂ 和 R₃ 各代表具有 4 至 12 个碳原子的直链或支链烷基，其中可包含芳香基团或不饱和烷基。 该分离介质适用于多种 DL-氨基酸的光学分辨，并具有优异的耐久性。
• Mechanistic Analysis of Muraymycin Analogues: A Guide to the Design of MraY Inhibitors
  作者：Tetsuya Tanino、Bayan Al-Dabbagh、Dominique Mengin-Lecreulx、Ahmed Bouhss、Hiroshi Oyama、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1021/jm200906r

  日期：2011.12.22

  The systematic structure activity relationship (SAX) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAX of the accessory urea peptide moiety indicated that it could be simplified. Our SAX study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop S. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs.