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The Allylic Oxidation of Geraniol Catalyzed by Cytochrome P‐450 Cath. , Proceeding with retention of configuration
Author(s) -
Fretz Heinz,
Woggon WolfDietrich,
Voges Rolf
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720227
Subject(s) - chemistry , allylic rearrangement , walden inversion , cytochrome , absolute configuration , stereochemistry , geraniol , catalysis , organic chemistry , chromatography , enzyme , essential oil
Incubation of the geraniols ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 1 and ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 1 with microsomal cytochrome P‐450 Cath. from the subtropical plant Catharanthus roseus (L.)G. D ON resulted in the formation of the chiral 8‐hydroxygeraniols ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 2 and ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 2 . Their absolute configuration was assigned on the basis of the 1 H‐decoupled 3 H‐NMR Spectra of the corresponding dicamphanates ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 9 and ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 9 , of which the configurations are established in relation to the synthetic reference samples. The results clearly indicate retention of configuration during the allylic oxidation of 1 .