A Great Improvement of the Enantioselectivity of Lipase-Catalyzed Hydrolysis and Esterification Using Co-Solvents as an Additive
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- Nishigaki Tomohiro
- Graduate School of Science and Technology, Kobe University
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- Yasufuku Yoshitaka
- Graduate School of Science and Technology, Kobe University
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- Murakami Sayuri
- Graduate School of Human Development and Environment, Kobe University
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- Ebara Yasuhito
- Graduate School of Human Development and Environment, Kobe University
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- Ueji Shin-ichi
- Graduate School of Human Development and Environment, Kobe University
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Addition of co-solvents such as tetrahydrofuran resulted in a great improvement of the enantioselectivity of lipase-catalyzed hydrolysis of butyl 2-(4-substituted phenoxy)propanoates in an aqueous buffer solution. On the other hand, lipase lyophilized from an aqueous solution containing the co-solvents catalyzed highly enantioselective esterification of 2-(4-substituted phenoxy)propionic acids, 2-(4-isobutylphenyl)propionic acid (ibuprofen), and 2-(6-methoxy-2-naphthyl)propionic acid (naproxen) in an organic solvent. An increase in the E value up to two orders of magnitude was observed for some substrates. The origin of the enantioselectivity enhancement caused by the co-solvent addition was mainly attributed to a significant deceleration in the initial reaction rate for the incorrectly binding enantiomer, as compared with that for the correctly binding enantiomer. From the results of FT-IR, CD, and ESR spectra, the co-solvent addition was also found to bring about a partial destruction of the tertiary structure of lipase.
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 81 (5), 617-622, 2008
公益社団法人 日本化学会
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詳細情報
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- CRID
- 1390282679120298240
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- NII論文ID
- 130004058902
- 10021075567
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- NII書誌ID
- AA00580132
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- ISSN
- 13480634
- 00092673
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- NDL書誌ID
- 9489818
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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