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CONVERSION OF A5-3/7-HYDROXYSTEROIDS A1,4-3-OXOSTEROIDS UNDER THE ACTION OF MYCOBACTERIA V. N. Shaposhnikov, A. A. Akhrem, and N. E. Voishvillo INTO UDC 542.91+547.92 We have effected the transformation of AS-3fi-hydroxysteroids of the androstane and pregnane series (I)-(IV), and also their acetates, into the corresponding A1,4-3-oxo derivatives by fermentation with Myco- bacteria. The transformation was carried out both on maize-glucose and on synthetic media. The prod- " uets were isolated by extraction from the culture liquid with chloroform and with purified by thin-layer chromatography. Of the 85 strains of Mycobacterium studied, the most active transforming agents proved to be bacteria of the species M. mucosum. The yields of the crude desired products that we obtained were 50-70%. The acetates of the As-3fi-hydroxysteroids are converted into A1,4-3-oxosteroids more rapidly than their unesterified analogs o COCHs COCH~ (\I--I r"\l-lt f\lt"]l /\y l H0 HO H0 (I) (II) (III) COCH3 I >o 1\/~1 H0 (iv) M. V. Lomonosov Moscow State University and Institute of Organic Chemistry, Academy of Sciences of the USSR. Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, p. 197, Jan- uary, 1969 Original article submitted September 30, 1968. 197

Conversion of δ5-3β-hydroxysteroids into δ1,4-3-oxosteroids under the action of mycobacteria

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C O N V E R S I O N O F A 5 - 3 / 7 - H Y D R O X Y S T E R O I D S

A 1 , 4 - 3 - O X O S T E R O I D S U N D E R T H E A C T I O N

O F M Y C O B A C T E R I A

V. N. S h a p o s h n i k o v , A. A. A k h r e m , a n d N. E. V o i s h v i l l o

I N T O

UDC 542.91+547.92

We have effected the t ransformat ion of AS-3fi-hydroxysteroids of the androstane and pregnane se r ies (I)-(IV), and also their acetates , into the corresponding A 1,4-3-oxo derivat ives by fermentat ion with Myco- bacter ia . The t ransformat ion was ca r r i ed out both on m a i z e - g l u c o s e and on synthetic media. The p rod- " uets were isolated by extract ion f rom the culture liquid with chloroform and with purified by th in- layer chromatography. Of the 85 s trains of Mycobacter ium studied, the most active t ransforming agents proved to be bacter ia of the species M. mucosum. The yields of the crude des i red products that we obtained were 50-70%. The acetates of the As-3fi-hydroxysteroids are converted into A 1,4-3-oxosteroids more rapidly than their unesterif ied analogs

o COCHs COCH~

( \ I - - I r"\l-lt f\lt"]l /\y l H0 HO H0

(I) (II) (III)

COCH3

I >o 1 \ / ~ 1

H0 (iv)

M. V. Lomonosov Moscow State Universi ty and Institute of Organic Chemis t ry , Academy of Sciences of the USSR. Transla ted f rom Izvest iya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, p. 197, Jan- uary , 1969 Original ar t ic le submitted September 30, 1968.

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