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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.
197