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Gallic Acid-Based Alkyl esters Synthesis in a Water-Free System by Celite-Bound Lipase of Bacillus licheniformis SCD11501

机译:地衣芽孢杆菌SCD11501的硅藻土结合脂肪酶在无水体系中合成没食子酸基烷基酯

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Gallic acid (3, 4, 5-trihydroxybenzoic acid) is an important antioxidant, anti-inflammatory, and radical scavenging agent. In the present study, a purified thermo-tolerant extra-cellular lipase of Bacillus licheniformis SCD11501 was successfully immobilized by adsorption on Celite 545 gel matrix followed by treatment with a cross-linking agent, glutaraldehyde. The celite-bound lipase treated with glutaraldehyde showed 94.8% binding/retention of enzyme activity (36 U/g; specific activity 16.8 U/g matrix; relative increase in enzyme activity 64.7%) while untreated matrix resulted in 88.1% binding/retention (28.0 U/g matrix; specific activity 8.5 U/g matrix) of lipase. The celite-bound lipase was successfully used to synthesis methyl gallate (58.2%), ethyl gallate (66.9%), n-propyl gallate (72.1%), and n-butyl gallate (63.8%) at 55 degrees C in 10 h under shaking (150 g) in a water-free system by sequentially optimizing various reaction parameters. The low conversion of more polar alcohols such as methanol and ethanol into their respective gallate esters might be due to the ability of these alcohols to severely remove water from the protein hydration shell, leading to enzyme inactivation. Molecular sieves added to the reaction mixture resulted in enhanced yield of the alkyl ester(s). The characterization of synthesised esters was done through fourier transform infrared (FTIR) spectroscopy and H-1 NMR spectrum analysis. (C) 2015 American Institute of Chemical Engineers
机译:没食子酸(3、4、5-三羟基苯甲酸)是重要的抗氧化剂,消炎剂和自由基清除剂。在本研究中,通过吸附在Celite 545凝胶基质上,然后用交联剂戊二醛处理,成功地纯化了纯化的地衣芽孢杆菌SCD11501的耐热细胞外脂肪酶。用戊二醛处理的与硅藻土结合的脂肪酶显示出94.8%的酶活性结合/保留(36 U / g;比活性16.8 U / g基质;酶活性相对增加64.7%),而未经处理的基质导致88.1%的结合/保留(脂肪酶为28.0 U / g基质;比活为8.5 U / g基质)。硅藻土结合的脂肪酶已成功用于在55°C下于10摄氏度下于5小时内合成没食子酸甲酯(58.2%),没食子酸乙酯(66.9%),没食子酸正丙酯(72.1%)和没食子酸正丁酯(63.8%)。通过依次优化各种反应参数,在无水系统中振荡(150 g)。更多极性醇(例如甲醇和乙醇)向其各自的没食子酸酯的低转化率可能是由于这些醇能够从蛋​​白质水合壳中严重去除水,从而导致酶失活。向反应混合物中加入分子筛可提高烷基酯的产率。合成酯的表征是通过傅立叶变换红外(FTIR)光谱和H-1 NMR光谱分析完成的。 (C)2015美国化学工程师学会

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