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Oxazolidinones are multifunctional compounds possessing diverse biological and pharmacological activity.Enzymatic synthesis of oxazolidin-2-one was studied using 2-aminoalochol and dimethyl carbonate and synthesis of 3-ethyl-1,3-oxazolidin-2-one was chosen as the model reaction using a variety of immobilized lipases; among which Candida antarctica lipase B (Novozyme 435) was the best catalyst. The reaction leads to the final product oxazolidin-2-one via methyl ethyl (2-hydroxyethyl) carbamate as theintermediate.The parameters affecting rate of reaction and the conversion of both steps were studied systematically and covered effects of agitation speed, solvent, catalyst loading and reaction temperature.A reaction mechanism was proposed wherein the coproduct methanol is generated in the first step leading to the formation of methyl ethyl (2-hydroxyethyl) carbamate as the intermediate which rearranges itself leading to the final products 3-ethyl-1,3-oxazolidin-2-one and methanol. The kinetic constant and activation energy were determined for each step of the reaction. The study was further extended to other 2-aminoalochols under optimized reaction conditions to prepare different oxazolidinones. This is a first report of its kind describing kinetics and mechanism of bimolecular consecutive enzyme catalyzed reactions. |
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愛與雨下: 金幣+1 2014-11-24 19:45:01
愛與雨下: 金幣+1 2014-11-24 19:45:01
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2樓2014-11-24 15:41:44
sudan789
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稍微改了一下。 惡唑烷酮類是一類多功能的化合物具有多種的生物學(xué)的和藥理學(xué)的應(yīng)用。研究了采用2-氨基醇和二甲基碳酸鹽來酶催化合成2-惡唑烷酮，選用3-乙基-1,3 -2-惡唑烷酮的合成作為使用多種的固定化脂肪酶的一個典型反應(yīng)；其中，念珠菌屬南極洲脂肪酶桿菌（novozyme 435）是最好的催化劑。反應(yīng)生成的最終產(chǎn)品2-惡唑烷酮是經(jīng)過甲基乙基（２-羥乙基）氨基甲酸鹽作為中間產(chǎn)物。系統(tǒng)地研究了影響反應(yīng)速度的參數(shù)，兩步的轉(zhuǎn)換，以及攪拌速度、溶劑、催化劑裝載和反應(yīng)溫度的綜合影響。提出了一種反應(yīng)機(jī)理，第一步中產(chǎn)生的副產(chǎn)品甲醇導(dǎo)致了甲基乙基（２-羥乙基）氨基甲酸鹽作為中間產(chǎn)物，這一中間產(chǎn)物自身重組成最終的產(chǎn)物3-乙基-1,3 -2-惡唑烷酮和甲醇。 動力學(xué)常數(shù)和活化能決定著分部反應(yīng)的每一步。研究進(jìn)一步延至其他2-氨基醇，用于在最佳化反應(yīng)條件下制備不同的惡唑烷酮類。這是第一次關(guān)于惡唑烷酮類種類描動力學(xué)和雙分子連續(xù)酶催化反應(yīng)的機(jī)理報道。 |
3樓2014-11-24 15:44:11
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