Microbiological transformations of steroids

Summary On fermentation of Reichstein's substance S with a culture ofStreptomyces albus 3006, 17,20-21-trihydroxy-4-pregnen-3-one was formed in high yield.     

Microbiological transformations of steroids

Summary A culture of Actinomyces albus 3006 is incapable of reducing the 20-keto group of 17,21-deoxy-⁴-3-keto steroids except when the substrate contains an oxygen function in the 11-position.We are deeply grateful to Dr. M. Shirasaka (Japan), Dr. P. Djassi (USA), and Dr. B. Camerino (Italy) for kindly providing samples of 7-hydroxyprogesterone, 15-hydroxyprogesterone, and 15-hydroxyprogesterone.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 11, pp. 2008–2015, November, 1964     

Microbiological transformations of steroids

Summary A culture ofActinomyces albus 3006 can effect the selective and stereospecific reduction of the C-20 keto group of corticosteroids and their ¹-dehydro analogs with formation of the corresponding 20-hydroxy compounds.     

Microbiological transformation of nitrogen-containing heterocyclic compounds. 3. Microbiological synthesis of hydroxy derivatives of 1-benzoylpiperidine and 1-benzoylpyrrolidine

The microbiological transformation of 1-benzoylpiperidine and 1-benzoylpyrrolidine by cultures of the fungi Aspergillus niger VKM F-1119 and Cunninghamella verticillala VKPM F-430 proceeds regio- and stereospecificall and leads respectively to the 4- and 3-hydroxy derivatives in 40–80% yield. The spectrometric properties of these compounds were studied.For Communication 2, see Biotekhnologiya, No. 4, 24, 1990.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 195–199, February, 1992.     

Synthesis of 19-hydroxysteroids I. New synthesis of 19-hydroxytestosterone

For obtaining 19-hydroxytestosterone from dehydroepiandrosterone a new scheme of synthesis has been developed the key stages of which are the reduction of the 17-keto group to a 17-alcohol, the functionalization of the 19-methyl group via the bromohydrin with the formation of a 6,19-epoxide, the selective hydrolysis of the free -acetoxy group, the conversion of the 3-hydroxy-5-bromo derivative into the ⁴-3-ketone, and the reductive cleavage of the 6,19-epoxide ring.Institute of Bioorganic Chemistry, Belorussian Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 672–678, November–December, 1992.     

Synthesis of 19-hydroxysteroids I. New synthesis of 19-hydroxytestosterone

For obtaining 19-hydroxytestosterone from dehydroepiandrosterone a new scheme of synthesis has been developed the key stages of which are the reduction of the 17-keto group to a 17-alcohol, the functionalization of the 19-methyl group via the bromohydrin with the formation of a 6β,19-epoxide, the selective hydrolysis of the free β-acetoxy group, the conversion of the 3β-hydroxy-5α-bromo derivative into the Δ⁴-3-ketone, and the reductive cleavage of the 6β,19-epoxide ring.     

Microbiological transformation products of 1,6-dimethylnaphthalene

Conclusions 6-Methyl-1-hydroxymethylnaphthalene, 6-methyl-1-naphthoic acid, and 6-hydroxymethyl-1-naphthoic acid were isolated and identified as being the microbiological transformation products of 1,6-dimethyl-naphthalene.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2619–2621, November, 1976.