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 Ohta

Research output: Contribution to journalArticle

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 (27-400 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.

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

Fingerprint

ursodeoxycholic acid
Ursodeoxycholic Acid
fatty acid esters
long chain fatty acids
bile acids
Bioactivity
Bile Acids and Salts
Lipase
bioactive properties
Esters
Fatty Acids
chemical derivatives
chenodeoxycholic acid
Pseudozyma antarctica
Derivatives
cholic acid
Chenodeoxycholic Acid
Cholic Acid
Acylation
acylation

Keywords

  • antibacterial activity
  • bile acid
  • Candida antarctica lipase
  • transesterification
  • ursodeoxycholic acid

ASJC Scopus subject areas

  • Food Science
  • Applied Microbiology and Biotechnology
  • Chemistry (miscellaneous)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology

Cite this

Efficient lipase-catalyzed preparation of long-chain fatty acid esters of bile acids : Biological activity and synthetic application of the products. / Sugai, Takeshi; Takizawa, Masahiro; Bakke, Mikio; Ohtsuka, Yoshikazu; Ohta, Hiromichi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 60, No. 12, 12.1996, p. 2059-2063.

Research output: Contribution to journalArticle

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