Tyrosinase catalysed biphenyl construction from flavan-3-ol substrates.
Mushroom tyrosinase catalysed oxidation of three flavan-3-ols, viz. catechin, fisetinidol and mesquitol, was conducted to construct biphenyl bonds. Exposure of the flavan-3-ols to tyrosinase and subsequent trapping of the o-quinone intermediates resulted in the formation of novel flavan-3-ol derivatives, the structures of which were elucidated by mono- and two-dimensional 1H-NMR experiments. Application of the methodology resulted in the improved synthesis of the natural flavan-3-ol dimer, mesquitol-[5-->8]-catechin, previously isolated from Prosopis glandulosa.
van Rensburg
W J
WJ
Department of Chemistry, University of the Orange Free State, Bloemfontein, South Africa. jvrensw@cem.nw.uovs.ac.za
Ferreira
D
D
Malan
E
E
Steenkamp
J A
JA
D000363:Agaricales / Q000201:enzymology*; D001713:Biphenyl Compounds / Q000737:chemistry / Q000378:metabolism*; D005419:Flavonoids / Q000378:metabolism*; D008958:Models, Molecular; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D013379:Substrate Specificity
D001713:Biphenyl Compounds; D005419:Flavonoids; C404987:flavan-3-ol; D014442:Monophenol Monooxygenase