Efficient Lipase-catalyzed Preparation of Long-chain Fatty Acid Esters of Bile Acids: Biological Activity and Synthetic Application of the Products

Takeshi Sugai, Masahiro Takizawa, Mikio Bakke, Yoshikazu Ohtsuka, Hiromichi Oht

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20 Citations (Scopus)

Abstract

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 (27–400μg/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.

Original languageEnglish
Pages (from-to)2059-2063
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume60
Issue number12
DOIs
Publication statusPublished - 1996 Jan

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Keywords

  • Antibacterial activity
  • Bile acid
  • Candida antarctica lipase
  • Transesterification
  • Ursodeoxycholic acid

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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