(R)-ibuprofen propyl ester | 157239-51-5

• 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 propyl ester
• 英文别名: (R)-ibuprofen 1-propyl ester；Propyl (I+/-R)-I+/--methyl-4-(2-methylpropyl)benzeneacetate；propyl (2R)-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 157239-51-5
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: QXWDAKBZLIENSO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙醇 、 布洛芬 在 optimized hybrid nanospheres immobilizing Rhizomucor miehei lipase 作用下， 以 异辛烷 为溶剂， 反应 72.0h， 以60%的产率得到
  参考文献：
  名称：

  用于手性生物转化的优化混合纳米球固定根毛霉脂肪酶

  摘要：

  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。

  DOI：

  10.1016/j.procbio.2015.11.020

文献信息

• One pot three-component reaction for covalent immobilization of enzymes: application of immobilized lipases for kinetic resolution of rac-ibuprofen
  作者：Mehdi Mohammadi、Somayyeh Gandomkar、Zohreh Habibi、Maryam Yousefi

  DOI：10.1039/c6ra11284f

  日期：——

  A one pot three-component reaction was used for the covalent immobilization of CALB and RML on epoxy-functionalized supports.

  使用一锅三组分反应将CALB和RML共价固定在环氧官能化支撑上。
• Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose
  作者：Maryam Yousefi、Mehdi Mohammadi、Zohreh Habibi

  DOI：10.1016/j.molcatb.2014.03.005

  日期：2014.6

  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.
• High Enantioselective Esterification of 2-Arylpropionic Acids Catalyzed by Immobilized Lipase from Candida antarctica: A Mechanistic Approach
  作者：Miguel Arroyo、Jose V. Sinisterra

  DOI：10.1021/jo00095a014

  日期：1994.8

  In order to study the mechanism of the enantioselective esterification of 2-arylpropionic acids catalyzed by lipases, a systematic study of the enzymatic activity of immobilized lipase from Candida antarctica (SP435A) in this reaction has been carried out. The main variables that have a positive effect on the reaction rate are temperature, amount of catalyst, reaction time, and an acid/alcohol molar ration of 1:1. The enzyme is enantioselective in the esterification of R(-) acid. Therefore the S(+) form, with pharmacological activity, can be prepared by enantioselective esterification of the racemate at temperatures below 24 degrees C and at conversions greater than 50%. The racemic temperature in the esterification of (+/-)-ibuprofen is 65.4 degrees C. In the esterification of (+/-)-2-phenylpropionic acid, isooctane is the best solvent. The reactivity observed is (+/-) ketoprofen > (+/-)-2-phenylpropionic acid > (+/-)-ibuprofen > (+/-)-naproxen = (+/-)-flurbiprofen in isobutyl methyl ketone saturated with water, a solvent in which all these antiinflammatory drugs are soluble and the enzymatic derivative is active. A qualitative model of the active site of this immobilized enzyme is described.
• Immobilization of Candida rugosa lipase onto magnetic beads for kinetic resolution of (R,S)-ibuprofen
  作者：Michał Piotr Marszałł、Tomasz Siódmiak

  DOI：10.1016/j.catcom.2012.03.027

  日期：2012.7

  Two commercially available lipases from Candida rugosa (CRL from Sigma-Aldrich Co. and OF from Meito Sangyo Co.) were immobilized onto glutaraldehyde-activated and EDC/sulfo-NHS-activated amine-terminated magnetic beads (MB). In this study a procedure for immobilization of lipase OF using EDC and sulfo-NHS onto the surface of magnetic particles was developed. The resulting "OF lipase enzymatic system" yielded good results of enantioselectivity (E = 19, ee(p) = 83%) and conversion (c = 42%) of the kinetic resolution of (R,S)-ibuprofen. Additionally, this procedure provides easy recovery and effective reuse of lipase OF, maintaining the enantioselectivity of the reaction on the same high level after five cycles. It was also demonstrated that the cross-linking reaction of lipases (CRL and OF) via glutaraldehyde onto magnetic support did not result in acceptable levels of conversion and enantioselectivity of the esterification reaction. Based on the results it should be noted that the immobilization technique we studied using EDC and sulfo-NHS onto MB could be potentially important for industrial application of kinetic resolution of non-steroidal anti-inflammatory drugs. (C) 2012 Elsevier B.V. All rights reserved.
• Esterification of (RS)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids
  作者：Fabiano Jares Contesini、Patrícia de Oliveira Carvalho

  DOI：10.1016/j.tetasy.2006.07.020

  日期：2006.8

  Four commercially available lipases and two native lipases from Aspergillus niger AC-54 and Aspergillus terreus AC-430 were used for the resolution of (RS)-Ibuprofen in systems containing the ionic liquids [BMIM][PF6] and [BMIM][BF4]. The lipases showed higher conversion in a two-phase system using [BMIM][PF6] and isooctane compared to that in pure isooctane. Although the best enzyme was a commercially available lipase from Candida rugosa (E = 8.5), another native lipase, produced in our laboratory, from A. niger gave better enantio selectivity (E = 4.6) than the other lipases tested (E = 1.9-3.3). After thorough optimization of several reaction conditions (type and ratios of isooctane/ionic liquid, amount of enzyme, and reaction time), the E-value of A. niger lipase (15% w/v) could be duplicated (E = 9.2) in a solvent system composed of [BMIM][PF6] and isooctane (1:1) after 96 h of reaction. (c) 2006 Elsevier Ltd. All rights reserved.