Microbial β-glycosylation of entacapone by Cunninghamella echinulata ATCC 9245

J Biosci Bioeng. 2012 May;113(5):611-3. doi: 10.1016/j.jbiosc.2012.01.004. Epub 2012 Feb 4.

Abstract

The purpose of this paper is to describe the glycosylation of entacapone by cultures of Cunninghamella echinulata ATCC 9245. This method is then applied in toxicological and pharmacological studies. The cultures were grown in a fluid PDSM medium for 7 days at 28°C. After purification by silica gel flash column chromatography, the (E)-2-cyano-N,N-diethyl-3-(4-hydroxy-3-nitro-5-(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)phenyl) acrylamide was identified by IR, mass spectroscopy and (1)H and (13)C NMR. The correct position and β-configuration of the glucose was determined through HSQC, HMBC and NOE experiments.

MeSH terms

  • Catechols / chemistry*
  • Catechols / metabolism*
  • Cunninghamella / metabolism*
  • Glucose / chemistry
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Nitriles / chemistry*
  • Nitriles / metabolism*

Substances

  • Catechols
  • Nitriles
  • entacapone
  • Glucose