Abstract
In order to investigate the reactivity of the homologs of homoallylic substrates, we examined the enzymatic reactions of E- or Z-3-methylhex-3-enyl diphosphate with farnesyl diphosphate using the undecaprenyl diphosphate synthase (UPS) of Micrococcus luteus B-P 26. E-3-methylhex-3-enyl diphosphate reacted with farnesyl diphosphate to give a chiral (4 S)-(2 Z,6 E,10 E,14 E)-4-ethyl-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol. However, the Z-isomer is not accepted as a substrate for the bacterial UPS at all.
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