7alpha-OH epimerisation of bile acids via oxido-reduction with Xanthomonas maltophilia

Steroids. 2002 Jan;67(1):51-6. doi: 10.1016/s0039-128x(01)00136-2.

Abstract

The microbial 7alpha-OH epimerisation of cholic, chenodeoxycholic, and 12-ketochenodeoxycholic acids (7alpha-OH bile acids) with Xanthomonas maltophilia CBS 827.97 to corresponding 7beta-OH derivatives with scarcity of oxygen is described. With normal pressure of oxygen the 7-OH oxidation products are obtained. No biotransformations are achieved in anaerobic conditions. The microbial 7alpha-OH epimerisation is achieved by oxidation of 7-OH function and subsequent reduction. Partial purification, in fact, of the enzymatic fraction revealed the presence of two hydroxysteroid dehydrogenases (HSDH) alpha- and beta-stereospecific together with a glycocholate hydrolase. On the basis of these results a further application is the microbial reduction of 6alpha-fluoro and 6beta-fluoro-3alpha-hydroxy-7-oxo-5beta-cholan-24-oic acid methyl esters to the corresponding 7alpha-OH and 7beta-OH derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bile Acids and Salts / chemistry*
  • Bile Acids and Salts / metabolism
  • Deoxycholic Acid / analogs & derivatives*
  • Deoxycholic Acid / chemical synthesis
  • Deoxycholic Acid / chemistry*
  • Hydroxysteroid Dehydrogenases / metabolism
  • Models, Chemical
  • Oxygen / metabolism
  • Spectrophotometry
  • Stenotrophomonas maltophilia / metabolism*
  • Ursodeoxycholic Acid / analogs & derivatives*
  • Ursodeoxycholic Acid / chemical synthesis
  • Ursodeoxycholic Acid / chemistry

Substances

  • 6-fluoro-3,7-dihydroxy-5-cholan-24-oic acid
  • 6-fluoro-ursodeoxycholic acid
  • Bile Acids and Salts
  • Deoxycholic Acid
  • Ursodeoxycholic Acid
  • Hydroxysteroid Dehydrogenases
  • Oxygen