Microbial monooxygenases applied to fragrance compounds

Biotransformation is an important tool in organic syntheses, especially for the production of chiral molecules and whenever chemical reactions are inefficient. Fragrance compounds were biotransformed by Trichosporum cutaneum CCT 1903 whole cells. Batch reactions with cis-jasmone (1), (R)-(−)-carvone (3), α- and β-ionones (4, 5) and (R)-(+)-limonene (10) produced 4-hydroxyjasmone (1a), 7,8-epoxyjasmone (1b), 7,8-dihydroxyjasmone (1c), (1S,2R,4R)-neoisodihydrocarveol (3a), (6R)-isoprenyl-(3R)-methyl-2-oxo-oxepanone (3b), (3R)-isopropenyl-6-oxoheptanoic acid (3c), 2,3-epoxy-(5R)-isopropenyl-2-methylcyclohexenol (3d), α-homo-cyclogeraniol (4a), 4-oxo-7,8-dihydro-β-ionone (5a), uroterpenol (10a) and (R)-(+)-limonene-1,2-diol (10b) as pure samples for spectroscopic identification (1H and 13C NMR, 1H,1H-gCOSY, HSQC, gHMBC). The stereochemical consequences of the transformations are also discussed.