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 7days 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 1H and 13C NMR. The correct position and β-configuration of the glucose was determined through HSQC, HMBC and NOE experiments.
biotransformation, Cunninghamella echinulata ATCC 9245, entacapone, entacapone glycoside, microbial glycosylation
NCBI PubMed ID: 22306315Publication DOI: 10.1016/j.jbiosc.2012.01.004Journal NLM ID: 100888800Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: de Oliveira V
Institutions: Laboratório de Bioconversão, Faculdade de Farmácia, Praça Universitária, Setor Universitário, Goiânia, Brazil, Laboratório de Química Farmacêutica Medicinal, Faculdade de Farmácia, Praça Universitária, Setor Universitário, Goiânia, Brazil, Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Goiânia, Brazil
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, HPLC, extraction, CC, cell growth, CLAE-EM/EM
Found