Efficient lipase-catalyzed preparation of long-chain fatty acid esters of bile acids: Biological activity and synthetic application of the products

Article abstract of DOI:10.1271/bbb.60.2059

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 (C₁₂-C₁₆) 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 46% yield and 9 steps.

Full text of DOI:10.1271/bbb.60.2059

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Bioscience, Biotechnology, and Biochemistry
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Efficient Lipase-catalyzed Preparation of Long-chain
Fatty Acid Esters of Bile Acids: Biological Activity and
Synthetic Application of the Products
Takeshi Sugaia, Masahiro Takizawaa, Mikio Bakkea, Yoshikazu Ohtsukaa & Hiromichi Ohtaa
a Department of Chemistry, Keio University, 3–14–1 Hiyoshi, Kohoku-ku, Yokohama 223,
Japan
Published online: 12 Jun 2014.
To cite this article: Takeshi Sugai, Masahiro Takizawa, Mikio Bakke, Yoshikazu Ohtsuka & Hiromichi Ohta (1996) Efficient
Lipase-catalyzed Preparation of Long-chain Fatty Acid Esters of Bile Acids: Biological Activity and Synthetic Application of
the Products, Bioscience, Biotechnology, and Biochemistry, 60:12, 2059-2063, DOI: 10.1271/bbb.60.2059
To link to this article: http://dx.doi.org/10.1271/bbb.60.2059
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