Journal of the Chemical Society. Perkin transactions I p. 355 - 358 (1996)
Update date:2022-08-11
Topics:
Shimoda, Kei
Ito, Diana I.
Izumi, Shunsuke
Hirata, Toshifumi
A reductase isolated from cultured cells of Nicotiana tabacum has been characterized and used in the reduction of a C=C bond adjacent to a carbonyl group. The stereochemistry of the latter reaction has been investigated by 2H NMR and mass spectroscopy. It was found that the reductase reduces stereospecifically the C=C bond of verbenone and carvone by syn addition of hydrogen from the re face at the β-position and the re face at the α-position to the carbonyl group; the hydrogen atoms participating in the enzymatic reduction at the α- and β-positions originate from the medium (H2O) and the pro-4S hydrogen of NADPH, respectively.
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