One step N-glycosylation by filamentous fungi biofilm in bioreactor of a new phosphodiesterase-3 inhibitor tetrazole

Bioorg Med Chem Lett. 2016 Jul 1;26(13):3177-3181. doi: 10.1016/j.bmcl.2016.04.085. Epub 2016 Apr 29.

Abstract

An efficient and rapid process for N-glycosylation of 5-(1-(3-fluorophenyl)-1H-pyrazol-4-yl)-2H-tetrazole-LQFM 021 (1), a new synthetic derivative of pyrazole with phosphodiesterase-3 (PDE-3) inhibitory action, vasorelaxant activity and low toxicity catalyzed by filamentous fungi biofilm in bioreactor was successfully developed. A maximum N-glycosyl yield of 68% was obtained with Cunninghamella echinulata ATCC 9244 biofilm in bioreactor with conditions of 25mgml(-1) of 1 in PDSM medium at 28°C for 96h. After extraction with ethyl acetate, the derivative was identified by Ultrahigh Resolution Mass Spectrometry and (1)H-(13)C HSQC/HMBC.

Keywords: Biofilm bioreactor; Cunninghamella; Glycosylation; LQFM 021; Phosphodiesterase-3 inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biofilms*
  • Bioreactors*
  • Cunninghamella / metabolism*
  • Dose-Response Relationship, Drug
  • Glycosylation
  • Molecular Structure
  • Phosphodiesterase 3 Inhibitors / chemistry
  • Phosphodiesterase 3 Inhibitors / metabolism
  • Phosphodiesterase 3 Inhibitors / pharmacology*
  • Phosphoric Diester Hydrolases / metabolism*
  • Structure-Activity Relationship
  • Tetrazoles / chemistry
  • Tetrazoles / metabolism
  • Tetrazoles / pharmacology*

Substances

  • Phosphodiesterase 3 Inhibitors
  • Tetrazoles
  • 1H-tetrazole
  • Phosphoric Diester Hydrolases