Composition of matter and process
AssigneeThe Upjohn Company
InventorsJohn C. Knight, Merle G. Wovcha
Life of this patent
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Abstract
Novel compounds prepared by microbial transformation using novel mutants to selectively degrade steroids with or without 17-alkyl side chains of from 2 to 10 carbon atoms, inclusive. These compounds can be used as intermediates to make useful steroids.
Claims12
A process for preparing a compound of the formula ##STR3## which comprises cultivating a mutant microorganism selected from the group consisting of Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces, said mutant being characterized by its ability to selectively degrade steroids with or without a 17-alkyl side chain of from 2 to 10 carbon atoms, inclusive, and accumulate predominantly 3a.alpha.-H-4.alpha.-[3'-propanol]-7a.beta.-methylhexahydro-1,5-indandione hemiketal and 3a.alpha.-H-4.alpha.-[3'-propanol]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone, and traces of 3a.alpha.-H-4.alpha.-[3'-propanal]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone hemiacetal and 3a.alpha.-H-4.alpha.-[3'-propionic acid]-5.alpha.-hydroxy-7a.beta.-methylhexahydro-1-indanone-.delta.-lactone in the fermentation beer, in an aqueous nutrient medium under aerobic conditions in the presence of a steroid with or without a 17-alkyl side chain containing from 2 to 10 carbon atoms, inclusive;
- and recovering said compound from the cultivated medium.
A process for preparing a compound of the formula ##STR4## which comprises cultivating a mutant microorganism selected from the group consisting of Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces, said mutant being characterized by its ability to selectively degrade steroids with or without a 17-alkyl side chain of from 2 to 10 carbon atoms, inclusive, and accumulate predominantly 3a.alpha.-H-4.alpha.-[3'-propanol]-7a.beta.-methylhexahydro-1,5-indandione hemiketal and 3a.alpha.-H-4.alpha.-[3'-propanol]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone, and traces of 3a.alpha.-H-4.alpha.-[3'-propanal]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone hemiacetal and 3a.alpha.-H-4.alpha.-[3'-propionic acid]-5.alpha.-hydroxy-7a.beta.-methylhexahydro-1-indanone-.delta.-lactone in the fermentation beer, in an aqueous nutrient medium under aerobic conditions in the presence of a steroid with or without a 17-alkyl side chain containing from 2 to 10 carbon atoms, inclusive;
- and recovering said compound from the cultivated medium.
A process for preparing a fermentation beer containing compounds of the following formulae ##STR5## which comprises cultivating a mutant microorganism selected from the group consisting of Arthrobacter, Bacillus, Brevibacterium, Corynebacterium, Nocardia, Protaminobacter, Serratia, and Streptomyces, said mutant being characterized by its ability to selectively degrade steroids with or without a 17-alkyl side chain of from 2 to 10 carbon atoms, inclusive, and accumulate predominantly 3a.alpha.-H-4.alpha.-[3'-propanol]-7a.beta.-methylhexahydro-1,5-indandione hemiketal and 3a.alpha.-H-4.alpha.-[3'-propanol]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone, and traces of 3a.alpha.-H-4.alpha.-[3'-propanal]-5.alpha.-hydroxy-7a.beta.-methylhexahyd ro-1-indanone hemiacetal and 3a.alpha.-H-4.alpha.-[3'-propionic acid]-5.alpha.-hydroxy-7a.beta.-methylhexahydro-1-indanone-.delta.-lactone in the fermentation beer, in an aqueous nutrient medium under aerobic conditions in the presence of a steroid with or without a 17-alkyl side chain containing from 2 to 10 carbon atoms, inclusive.
Dependencies are inferred from the claim text.