(R)-ibuprofen butyl ester | 160391-17-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-ibuprofen butyl ester
• 英文别名: Butyl (I+/-R)-I+/--methyl-4-(2-methylpropyl)benzeneacetate；butyl (2R)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 160391-17-3
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: JMYISEMZJYEMCF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  butyl 2-(4-isobutylphenyl)propanoate 在 Candida rugosa lipase immobilized on octyl sepharose 作用下， 以 aq. phosphate buffer 、 异辛烷 为溶剂， 反应 72.0h， 以97.1%的产率得到
  参考文献：
  名称：

  Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose

  摘要：

  Here we report the stereoselective hydrolysis of racemic esters catalyzed by Candida rugosa lipase (CRL) and Rhizopus oryzae lipase (ROL) immobilized on octyl-sepharose via physical adsorption. Hydrophobic immobilization caused to almost six fold hyperactivation with 229.2 and 81.3 U/mg enzyme for immobilized CRL and ROL, respectively (13.2 and 48.75 U/mg for corresponding free enzyme). Based on the preliminary results, CRL was chosen for further investigation. The performance and yield of the reaction were evaluated as a function of the critical reaction parameters such as temperature, enzyme to substrate ratio and organic co-solvent. An increase in the temperature resulted to decrease in enantioselectivity of hydrolysis reaction. The hydrolysis reactions were carried out in presence of two organic solvents; n-hexane and isooctane. Generally n-hexane was a better co-solvent compared to isooctane. High enantioselective hydrolysis of the racemic esters (yielding S(+) ibuprofen; ee >= 95%) can be achieved using the immobilized CRL. Among various esters the kinetic resolution of ibuprofen butyl ester yielded the best results (E value 70 and 74; conversion 14.6 and 8.9 in n-hexane and isooctane, respectively). The immobilized derivatives were re-used in four cycles and showed little decrease in enantiomeric excess of (S)-ibuprofen. 96.7 ee(p) and conversion 14.6 in first cycle reached to 90.5 ee(p) and conversion 11.3 in the forth cycle. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.03.005

文献信息

• Optimized hybrid nanospheres immobilizing Rhizomucor miehei lipase for chiral biotransformation
  作者：F. Verri、U. Diaz、A. Macario、A. Corma、G. Giordano

  DOI：10.1016/j.procbio.2015.11.020

  日期：2016.2

  miehei lipase into hybrid nanospheres containing a liposomal core was reported. Organic internal liposomal enzyme phase was protected by inorganic silica matrix, obtained with and without surfactant, that stabilizes the internal organic phase and isolates and protects the bioactive molecules. The optimized heterogeneous catalyst thus prepared was used for enantioselective esterification of (R,S)-ibuprofen

  摘要 在这项研究中，报道了将根毛霉脂肪酶固定到含有脂质体核心的杂化纳米球中。有机内部脂质体酶相由无机二氧化硅基质保护，使用和不使用表面活性剂获得，稳定内部有机相并分离和保护生物活性分子。由此制备的优化的多相催化剂用于(R,S)-布洛芬的对映选择性酯化。研究了几种催化参数对混合纳米球活性的影响（溶剂类型、醇的性质、反应温度等）。多相生物催化剂在 37 °C 下表现最佳，使用异辛烷作为溶剂，1-丙醇作为醇（酯产率在 78% 到 93% 之间）。观察到酶固定的杂化纳米球相对于游离形式的高活性和稳定性（最多 9 个反应循环）。R. miehei 脂肪酶，无论是游离形式还是固定形式，在所有测试的反应条件下，仅与 (R,S)-布洛芬的 S(+) 对映异构体反应。
• Lipase-immobilized magnetic chitosan nanoparticles for kinetic resolution of (R,S)-ibuprofen
  作者：Tomasz Siódmiak、Marta Ziegler-Borowska、Michał Piotr Marszałł

  DOI：10.1016/j.molcatb.2013.04.008

  日期：2013.10

  Chitosan (CS)-poly[N-benzyl-2-(methacryloxy)-N,N-dimethylethanaminium bromide] coated magnetic nanoparticles were prepared by co-precipitation method via epichlorohydrin CS cross-linking reaction and were used in the kinetic resolution of (R,S)-ibuprofen by enantioselective esterification. Enzyme immobilized onto the surface of the new magnetic supports with the use of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC)/N-hydroxysulfo-succinimide sodium salt (sulfo-NHS) procedure demonstrated high catalytic activity that enabled us to obtain (S)-methyl ester of ibuprofen with high enantioselectivity (E = 50.6). The chiral compounds that resulted from the application of magnetic nanoparticles were analyzed with the use of chiral stationary phases. It should be emphasized that the main advantage of the support is the possibility to magnetically recovery and effective separation (even up to 5 s) from the reaction mixture with the use of magnet. The properties of magnetic particles allow for better optimization and may reduce the total costs of the esterification reaction of ibuprofen. Moreover, the application of lipase-immobilized magnetic supports enables to maintain high enantioselective activity after repeated use. (c) 2013 Elsevier B.V. All rights reserved.