Microbial β-glycosylation of entacapone by Cunninghamella echinulata ATCC 9245.
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.
Laboratório de Bioconversão, Faculdade de Farmácia, 1ª Avenida esquina c/ Praça Universitária, S/N. Postal Box 131, Setor Universitário, CEP: 74.605-220, Goiânia, GO, Brazil.
Keyla R M D
KR
Lustosa
Ricardo
R
Menegatti
Rodolpho C
RC
Braga
Luciano M
LM
Lião
Valéria
V
de Oliveira
D002396:Catechols / Q000737:chemistry* / Q000378:metabolism*; D020093:Cunninghamella / Q000378:metabolism*; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009570:Nitriles / Q000737:chemistry* / Q000378:metabolism*
D002396:Catechols; D009570:Nitriles; C071192:entacapone; D005947:Glucose