Efficient Lipase-catalyzed Preparation of Long-chain Fatty Acid Esters of Bile Acids: Biological Activity and Synthetic Application of the products
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概要
- 論文の詳細を見る
A highly regioselective (3-position) and efficient (quantitative yield) acylation of bile acids catalyzed by immobilized Candida antarctica lipase was established. Methyl cholate derivatives acylated with long-chain fatty acids (C_<12>-C_<16>) showed an inhibitory effect on the growth of some strains of Gram-positive and -negative bacteria (27-400 μg/ml). The anti-bacterial activity was slightly weaker than has been observed for methyl cholate, while the increased lipophilicity and lower melting points of the present derivatives are well suited for a potential germicide which would be safe and be topically applied. This enzyme-catalyzed transesterification is also demonstrated as an expeditious route to ursodeoxycholic acid, in respect of the regioselective introduction of acyl protecting groups on the hydroxyl groups of the intermediates. 7-Ketolithocholic acid, a known direct precursor of ursodeoxycholic acid, was obtained from cholic acid via chenodeoxycholic acid in a 460% yield and 9 steps.
- 社団法人日本農芸化学会の論文
- 1996-12-23
著者
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OHTSUKA Yoshikazu
Department of Pediatrics and Adolescent Medicine, Juntendo University School of Medicine
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須貝 威
慶應義塾大学理工学部
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Ohta H
Okayama Univ. Okayama
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Ohta H
Department Of Bioscience And Informatics Center For Life Science And Technology Keio University
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Ohta H
Department Of Chemistry Faculty Of Science And Technology Keio University
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Ohta H
Department Of Chemistry Keio University
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Ohta Hiromichi
Department Of Chemistry Faculty Of Science And Technology Keio University
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Ohtsuka Y
Keio Univ. Yokohama
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Ohta H
Keio Univ. Kanagawa
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Sugai Tomoharu
Department Of Bioresource Engineering Faculty Of Agriculture Yamagata University
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SUGAI Takeshi
Department of Chemistry, Faculty of Science and Technology, Keio University
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Ohtsuka Yoshikazu
Department Of Chemistry Keio University
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Ohta H
Department Of Food And Nutrition Nakamura Gakuen University
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Ohta Hiromichi
Department Of Applied Chemistry School Of Engineering Nagoya University
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BAKKE Mikio
Department of Chemistry, Keio University
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TAKIZAWA Masahiro
Department of Chemistry, Keio University
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Bakke Mikio
Department Of Chemistry Keio University
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Okazaki Hanako
Department Of Chemistry Keio University
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Sugai Takeshi
Department Of Agricultural Chemistry The University Of Tokyo
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Takizawa Masahiro
Department Of Chemistry Keio University
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Takizawa Masahiro
Department Of Applied Physics Waseda Uiversity
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