A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive |
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| Affiliation: | 1. Graduate School of Science and Technology, Kobe University, Nada, Kobe 657-8501, Japan;2. Division of Natural Environment and Bioorganic Chemistry, Faculty of Human Development and Sciences, Kobe University, Nada, Kobe 657-8501, Japan;1. Fujian Province Key Laboratory of Modern Analytical Science and Separation Technology, Minnan Normal University, Zhangzhou 363000, China;2. College of Chemistry and Environment, Minnan Normal University, Zhangzhou 363000, China;1. Institute of Physics, Academy of Sciences of the Czech Republic, Cukrovarnická 10, 162 00 Prague 6, Czech Republic;2. Laboratoire de Physique des Interfaces et des Couches Minces (LPICM), École Polytechnique, CNRS, F-91128 Palaiseau, France;1. Department of Physics, Lal Bahadur Shastri Mahavidyalaya, Dharmabad, Dist. Nanded 431809, MS, India;2. Department of Electronics, Lal Bahadur Shastri Mahavidyalaya, Dharmabad, Dist. Nanded 431809, MS, India;3. School of Physical Sciences, S.R.T.M.University, Nanded 431606, MS, India;1. College of Physics, Jilin University, Changchun, 2699 Qianjin St., Changchun 130012, People''s Republic of China;2. Institute of High Technologies, Taras Shevchenko National University of Kyiv, 64 Volodymyrska, 01033 Kyiv, Ukraine;3. V. Lashkaryov Institute of Semiconductor Physics, National Academy of Sciences of Ukraine, 41 Prosp. Nauky, 03680 Kyiv, Ukraine;4. Corporation Science Park Taras Shevchenko University of Kyiv, 60, Volodymyrska Str., 01033 Kyiv, Ukraine;1. The College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, PR China;2. The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan 450052, PR China |
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| Abstract: | The addition of sodium dodecyl sulfate (SDS) resulted in a dramatic improvement of the enantioselectivity of the lipase-catalyzed hydrolysis of racemic butyl 2-(4-substituted phenoxy)propanoates, racemic butyl 2-(4-isobutylphenyl)propanoate, and racemic butyl 2-(6-methoxy-2-naphthyl)propanoate in an aqueous buffer solution. An increase in the E value by up to two orders of magnitude was observed for some esters. As to the effects of SDS on the structure of a lipase, FT-IR and fluorescence measurements suggest some conformational change and/or an increase of the flexibility of the lipase, although the native secondary structure of the lipase is held even in the presence of 100 mM SDS. The origin of the enantioselectivity enhancement brought about by the addition of SDS is briefly discussed on the basis of the values of the initial rates obtained for each enantiomer of the substrate. |
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