Bulletin of the Chemical Society of Japan p. 869 - 878 (1988)
Update date:2022-08-05
Topics:
Hamada, Hiroki
The biotransformation of the enantiomeric pairs of p-menthane and bicyclo<2.2.1> and <3.1.1>heptane derivatives with the cultured cells of Nicotiana tabacum was investigated.It was found that (i) the cultured cells discriminate the enantiomers of p-menthan-2-ol and bicyclo<2.2.1>heptan-2-ol and bicyclo<3.1.1>heptan-3-ol derivatives, and enantioselectively convert these alcohols to the corresponding ketones, (ii) the cells reduce the carbonyl group of p-methan-2-one derivatives to a high extent, but not that of p-menthan-3-ones, and (iii) the cells discriminate the enantiomers of bicyclo<3.1.1>hept-2-en-4-one (verbenone) and enantioselectively reduce the C-C double bond of the (1S,5S)-enantiomer.
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