Biochemische Oxydationen in der Sterin- und Sexualhormonreihe durch Micrococcus Dehydrogenans. III. Mitteilung. Umwandlung desΔ5-Androstendiols-(3,17) in Testosteron

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Abstract
Two kinds of bacteria, Bacterium steroidiclasium and Micrococcus dehydrogenans, are isolated from suspensions of compressed bakers'' yeast available in Mailand. The former bacteria catabolize steroids, such as dehydroandro-sterone and androstenedione, to such an extent that no polycyclic end products can be detected in the reaction mixtures. The latter bacteria are Gram-positive, 0.3-0.55 u in diam., do not form gas with glucose, lactose, levulose, arabinose, etc., do not show peptonization in milk and do not liquify gelatin. The bacteria are able to dehydrogenate the secondary alcohol group in the 3-position to the carbonyl group. In a 1- l. flasks are placed 450 ml. yeast extract, 75 ml. M/5 KH2PO4 and 75 ml. Af/5 Na2HPO4 soln. The soln. is sterilized, inoculated with M. dehydrogenans, and aerated with a stream of sterile air for 24 hrs. at 35[degree]. The bacteria multiply. A sterile soln. of 250 mg. [DELTA]5-andro-stenediol-(3,17) in 25 ml. alcohol is added dropwise, and the aeration continued 3 days at 35[degree]. Sterile water is added occasionally to keep the vol. constant. After the oxidation is completed, the mixture is extracted with ether, which is washed with water, and dilute NaOH soln., and concd. The ether residue is decomposed with the Girard Ketone Reagent T and a ketone fraction isolated which is crystallized 3 times from dilute acetone and 160 mg. of testosterone, m. 151[degree], obtained. From the mother liquors of the crystallizations are isolated 10 mg. androstenedione, m. 167[degree]-168[degree]. The bacteria also convert dehydroandrosterone to androstenedione, pregnenolone to progesterone, nor-choIestenol-(3)-on-(25) to norcholestenedione-(3,25) and 17-ethinylandrostenediol-(3,l7) to pregnene-in-ol-(17)-on-(3).

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