STEREOCHEMISTRY OF REDUCTION OF THE ENDOCYCLIC DOUBLE BOND OF (-)-CARVONE WITH THE ENZYME PREPARATION FROM CULTURED CELLS OF NICOTIANA TABACUM

Article abstract of DOI:10.1016/0031-9422(89)80341-3

The stereochemistry of the reduction of the endocyclic C-C double bond of (4R)-(-)-carvone with an enzyme preparation from cultured cells of Nicotiana tabacum was investigated by (2)H NMR and mass spectroscopy.It was found that: (i) the enzyme preparation regioselectively reduces only the endocyclic double bound; (ii) the reduction occurs stereospecifically by anti addition of hydrogen from the si face at C-1 and the re face at C-6 of carvone, resulting in the formation of (1R,4R)-(+)-dihydrocarvone; (iii) the hydrogen atoms participating in the enzymatic reduction at C-1 and C-6 originate from the medium and the pro-4R hydrogen of NADH, respectively.Key Word Index - Nicotiana tabacum; Solanaceae; cultured cells; enzymatic reduction; stereochemistry; carvone.