ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The hydroxylation of geraniol (8) by cytochrome P-450 (P-450Cath.) from the subtropical plant Catharanthus roseus (L.) G. DON was optimised to give 8-hydroxygeraniol (9) as the single product in 35% yield. Incubations of different 13C- and 2H-labelled geraniols revealed that H-abstraction is completely regioselective in favour of the CH3 group trans to the chain at C(6) of 8. An intramolecular isotope effect kH/kD = 8.0 was determined, suggesting that H-abstraction is one of the major rate-contributing steps; however, the intermolecular isotope effect was surprisingly inverse at low conversion kH/kD = 0.50, indicating the existence of rate-contributing steps preceding the first irreversible, isotope-sensitive reaction in the sequence.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690822
