Streptomyces roseochromogenes

Figure 9.6 An example of 16a-hydroxylation catalysed by Streptomyces roseochromogenes. Commercial 16a-hydroxylations are carried out by Squibb.

This is a 16a-hydroxylation, usually carried out using Streptomyces roseochromogenes. 

Clark et al. [81] determined the time course of A-acetylation of primaquine by Streptomyces roseochromogenous and Streptomyces rimosus by quantitative high performance liquid chromatographic analyses of the culture broths. The A-5-bistri-fluoroacetyl derivative of primaquine was used as an internal standard in the analysis for the quantitation of primaquine A-acetate in microbial culture broths. S. roseochromogenous forms the highest level of primaquine A-acetate at 24—36 h after substrate addition, while S. rimosus is slower in its acetylation, peaking at 3 days after substrate addition. The formation of a novel dimeric compound from the reaction of primaquine with 8-(4-phthalimido-l-methylbutylamino)-6-methoxy quinoline is also reported. 

Scheme 13. Metabolism of lysergic acid amide congeners by Streptomyces roseochromogenes. 

Streptomyces lavendulae SEN-158 (1-deoxynojirimycin), 106 Streptomyces lydicus PA-5726 (galactonojirimycin), 141 Streptomyces nojiriensis sp. SF-426 (nojirimycin), 105 Streptomyces roseochromogenes (anisomycin), 46... 

Figure 14 Metabolism of lysergic acid dialkylamide homologues by Streptomyces roseochromogenes...

Ishii, H., Hayashi, M., Niwaguchi, T. and Nakahara, Y. (1979b) Studies on lysergic acid diethylamide and related compounds. IX. Microbial transformation of amides related to lysergic acid diethylamide by Streptomyces roseochromogenes. Chem. Pharm. Bull., 27, 3029-3038. 

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