Mycobacterium rhodochrous

The metabolic functionalization of cannabinoids is of continuing interest (c/. Vol. 4, p. 71 Vol. 7, p. 50). A -THC may be hydroxylated at C-4 using Mycobacterium rhodochrous (together with aromatization) or at C-4" of the side-chain with Bacillus cereus or may be oxygenated at C-5 with Streptomyces species. A -THC has been hydroxylated in both the ring system and the side-chain with Pellicularia filamentosa and Streptomyces lavendulae, and further evidence in favour of in vivo epoxy metabolites and derivatives in the mouse has been presented (cf. Vol. 4,... 

The oxidation of racemic fenchone by a Corynebacterium sp.[7<>1 (reclassified as Mycobacterium rhodochrous), an organism which grows at the expense of either (+)- or (-)- camphor, has also been reported. This was shown to lead, in a 45% yield, to a 90/10 mixture of 1,2 and 2,3-fencholides, as shown in Fig. 16.5-12. This result contrasts with the chemical oxidation of fenchone with peracetic acid, where 2,3-fencholide is the major product in a 40/60 mixture. Accumulation of these lactones is a priori surprising as compared with the total degradation of the structurally similar camphor substrate. However this may simply be due to the fact that this lactone, unlike that formed from camphor, is chemically stable in the medium. Of course, one has also to assume that, here again, the strain is devoid of any lactone hydrolase. This bioconversion was the first gram-scale preparative report... 

Camphor Mycobacterium rhodochrous NCIMB 9784 Pseudomonas putida NCIMB 10007 Kay et al. (1962) Conrad et al. (1961)... 

Confirmatory evidence for the oxidation of benzene according to Eq. (10) has been obtained with whole cell cultures and sonic extracts of soil isolates of Pseudomonas aeruginosa and Mycobacterium rhodochrous (Marr and Stone, 1961). 

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