Process for preparing an indenedione and a mycobacterium culture therefor
AssigneeThe Upjohn Company
InventorsJohn C. Knight, Merle G. Wovcha
Life of this patent
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Abstract
A process for the microbiological conversion of steroids to (2+)-(7aS) 2,3,7,7-tetrahydro-7a-methyl-(1H)-indene-1,5(6H)-dione, hereinafter referred to as the indenedione.
Claims5
A process for preparing (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5(6H)-dione which comprises cultivating Mycobacterium fortuitum NRRL B-15026 in a fermentation beer, in an aqueous, nutrient medium under aerobic conditions in the presence of a steroid with or without 17-hydrocarbon side chains to produce (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5(6H)-dione in the fermentation beer and isolating (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5(6H)-dione from the fermentation beer.
A process for preparing (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5-(6H)-dione which comprises (a) cultivating Mycobacterium fortuitum NRRL B-15026 in an aqueous nutrient medium under aerobic conditions in the presence of a steroid with or without 17-hydrocarbon side chains to produce (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5-(6H)-dione in a fermentation beer;
- (b) extracting a mixture from the beer with methylene chloride;
- (c) concentrating the mixture to give an oil;
- (d) subjecting the oil to chromatography;
- (e) treating (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene 1,5-(6H)-dione obtained by chromatography with activated carbon;
- (f) crystallization of (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl (1H)-indene-1,5-(6H)-dione from a solvent.
A biologically pure culture of mutant of Mycobacterium fortuitum, having the deposit accession number NRRL B-15026, which is characterized by its ability to selectively degrade steroids with or without 17-hydrocarbon side chains, in the presence of an aqueous nutrient medium and aerobic conditions, and to accumulate (2+)-(7aS)-2,3,7,7a-tetrahydro-7a-methyl-(1H)-indene-1,5(6H)-dione in the fermentation beer.
Dependencies are inferred from the claim text.