(R)-3-hydroxy-14-methylpentadecanoic acid | 799830-55-0

• 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: (R)-3-hydroxy-14-methylpentadecanoic acid
• 英文别名: (3R)-3-hydroxy-14-methylpentadecanoic acid
• CAS: 799830-55-0
• 化学式: C₁₆H₃₂O₃
• 分子量: 272.428
• InChiKey: ZZUNWCHKAFUBIS-OAHLLOKOSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  400.1±28.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-14-methylpentadecanoic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 4-二甲氨基吡啶 、 苯硅烷 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 39.25h， 生成 (R)-3-((2S,3S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)-4-(cyclohexyloxy)-4-oxobutyloxy)-14-methylpentadecanoic acid
  参考文献：
  名称：

  Total Synthesis of Plusbacin A₃:  A Depsipeptide Antibiotic Active Against Vancomycin-Resistant Bacteria

  摘要：

  Plusbacin A(3) is a depsipeptide antibiotic isolated from Pseudomonas sp. Although the stereochemistry at the lactone stereocenter had not been determined, biological evaluation of this compound demonstrated it to have promising antibacterial activity against vancomycin-resistant enterococci. Its mechanism of action remains to be conclusively established, but it is believed to exert its antibiotic effect through inhibition of bacterial cell wall biosynthesis. In this paper, we describe the first total synthesis of plusbacin A(3) and assign the stereochemistry for the remaining unassigned lactone stereocenter.

  DOI：

  10.1021/ja068455x
• 作为产物：
  描述：

  11-methyl-dodec-1-ene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 (R)-3-hydroxy-14-methylpentadecanoic acid
  参考文献：
  名称：

  Total Synthesis of Plusbacin A₃:  A Depsipeptide Antibiotic Active Against Vancomycin-Resistant Bacteria

  摘要：

  Plusbacin A(3) is a depsipeptide antibiotic isolated from Pseudomonas sp. Although the stereochemistry at the lactone stereocenter had not been determined, biological evaluation of this compound demonstrated it to have promising antibacterial activity against vancomycin-resistant enterococci. Its mechanism of action remains to be conclusively established, but it is believed to exert its antibiotic effect through inhibition of bacterial cell wall biosynthesis. In this paper, we describe the first total synthesis of plusbacin A(3) and assign the stereochemistry for the remaining unassigned lactone stereocenter.

  DOI：

  10.1021/ja068455x

文献信息

• Total Synthesis of Plusbacin A₃ and Its Dideoxy Derivative Using a Solvent-Dependent Diastereodivergent Joullié–Ugi Three-Component Reaction
  作者：Akira Katsuyama、Fumika Yakushiji、Satoshi Ichikawa

  DOI：10.1021/acs.joc.8b00038

  日期：2018.7.6

  which is a depsipeptide with antibacterial activity, and its dideoxy derivative are described. To establish an efficient synthetic route of 1, a solvent-dependent diastereodivergent Joullié–Ugi three-component reaction (JU-3CR) was used to construct trans-Pro(3-OH) in a small number of steps. Two strategies were investigated toward the total synthesis. In the first synthetic strategy, the key steps were

  描述了我们对plusbacin A 3（1）的合成研究的全部细节，plusbacin A 3（一种具有抗菌活性的二肽）及其双脱氧衍生物。为了建立有效的1合成路线，使用了溶剂依赖性非对映异构的Joullié-Ugi三组分反应（JU-3CR ），可通过少量步骤构建反式Pro（3-OH）。针对总合成研究了两种策略。在第一个合成策略中，关键步骤是反式JU-3CR和合成最后阶段的大环内酯化。在1,1,1,3,3,3-六氟异丙醇中使用烷基异氰化物的JU-3CR提供了反式产物和片段的偶联以制备大环化前体进行得很顺利。但是，尝试进行大内酯化不能提供所需的产物。然后，研究了在初始阶段包括酯化的第二种策略。使用可转换的异氰酸酯检查了构建反式-Pro（3-OH）的方法，该可转换的异氰酸酯可转换为以下酰胺化所需的羧酸。通过使用羟基-Asp衍生物和相应的醇的分子间偶联来实现酯键的形成，并且酰胺化得到线性的二肽。线性
• Total Synthesis and Antibacterial Investigation of Plusbacin A₃
  作者：Akira Katsuyama、Atmika Paudel、Suresh Panthee、Hiroshi Hamamoto、Toru Kawakami、Hironobu Hojo、Fumika Yakushiji、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.7b01629

  日期：2017.7.21

  The total synthesis of plusbacin A3 (1) has been accomplished using a solvent-dependent diastereodivergent Joullié–Ugi three-component reaction (JU-3CR) as a key step. Two trans-3-hydroxy-l-proline residues were constructed by combining the JU-3CR with a convertible isocyanide strategy. Subsequent peptide coupling and macrolactamization afforded plusbacin A3. Investigating the antibacterial activity

  正构细菌A 3（1）的总合成已通过溶剂依赖性非对映异构的Joullié-Ugi三组分反应（JU-3CR）作为关键步骤完成。通过将JU-3CR与可转换的异氰化物策略结合，可构建两个反式-3-羟基-1-脯氨酸残基。随后的肽偶联和大内酰胺化提供了plusbacin A 3。与1的双脱氧类似物相比，研究1的抗菌活性表明，苏-β-羟基天冬氨酸残基对于抗菌活性是必不可少的。值得注意的是，在S中产生抗药性的可能性很小。金黄色葡萄球菌对抗细菌A 3。
• Structural Identification of Antibacterial Lipids from Amazonian Palm Tree Endophytes through the Molecular Network Approach
  作者：Morgane Barthélemy、Nicolas Elie、Léonie Pellissier、Jean-Luc Wolfender、Didier Stien、David Touboul、Véronique Eparvier

  DOI：10.3390/ijms20082006

  日期：——

  A library of 197 endophytic fungi and bacteria isolated from the Amazonian palm tree Astrocaryum sciophilum was extracted and screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Four out of five antibacterial ethyl acetate extracts were also cytotoxic for the MRC-5 cells line. Liquid chromatography coupled to tandem mass spectrometry (UPHLC-HRMS/MS) analyses combined with molecular networking data processing were carried out to allow the identification of depsipeptides and cyclopeptides responsible for the cytotoxicity in the dataset. Specific ion clusters from the active Luteibacter sp. extract were also highlighted using an MRSA activity filter. A chemical study of Luteibacter sp. was conducted leading to the structural characterization of eight fatty acid exhibiting antimicrobial activity against MRSA in the tens of µg/mL range.

  从亚马逊棕榈树Astrocaryum sciophilum中分离出的197株内生真菌和细菌库被提取并筛选其对甲氧西林耐药金黄色葡萄球菌（MRSA）的抗菌活性。其中五个抗菌乙酸乙酯提取物中有四个对MRC-5细胞系也具有细胞毒性。采用液相色谱-高分辨质谱（UPHLC-HRMS/MS）分析，结合分子网络数据处理，可确定引起数据集细胞毒性的依赖肽和环肽。利用MRSA活性过滤器，还突出了活性Luteibacter sp.提取物中的特定离子簇。对Luteibacter sp.的化学研究导致了8种脂肪酸的结构表征，这些脂肪酸在十几微克/毫升的范围内对MRSA具有抗菌活性。
• Solid-Phase Total Synthesis of Plusbacin A₃
  作者：Kazuki Takashina、Akira Katsuyama、Rintaro Kaguchi、Kazuki Yamamoto、Toyotaka Sato、Satoshi Takahashi、Motohiro Horiuchi、Shin-ichi Yokota、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.2c00667

  日期：2022.3.25

  The total synthesis of the depsipeptide natural product plusbacin A3 (1) utilizing solid-phase peptide synthesis (SPPS) was disclosed. A 3-hydroxy-proline derivative compatible with Fmoc SPPS was prepared by a diastereoselective Joullié–Ugi three-component reaction (JU-3CR)/hydrolysis sequence. After peptide elongation on the solid support, cleavage of the peptide from the resin, followed by macrolactamization

  公开了使用固相肽合成(SPPS)的缩肽天然产物加杆菌素A 3 ( 1 )的全合成。通过非对映选择性 Joullié-Ugi 三组分反应 (JU-3CR)/水解序列制备了与 Fmoc SPPS 相容的 3-羟基-脯氨酸衍生物。在固相支持物上肽延伸后，肽从树脂上裂解，然后大环内酰胺化和整体去保护，得到plusbacin A 3 ( 1 )。