Introduction of a 16 alpha-hydroxyl function into estrone by Streptomyces roseochromogenes.
Streptomyces roseochromogenes (NRRL B-1233) converted estrone predominantly into its 16 alpha-hydroxyl derivative. Chemical and spectroscopic (UV, IR, NMR, MS) methods were used in establishing the structure and strereochemistry of the oxidation product. The product was assigned as 16 alpha-hydroxyestrone (yield, 17%). No other oxidation product was detected in this experiment. An interrelationship between cell growth and 16 alpha-hydroxy-estrone formation was observed. Also, 16 alpha-hydroxylation of estrone was observed in resting cells. 16 alpha-Hydroxylase showed good activity at 3.7 X 10(-4)M of estrone concentration and was completely inhibited by 1.1 X 10(-3)M. These results indicate the presence of a constitutive 16 alpha-hydroxylase in the organism investigated.
D055598:Chemical Phenomena; D002621:Chemistry; D004970:Estrone / Q000031:analogs & derivatives* / Q000378:metabolism*; D006894:Hydroxyestrones / Q000096:biosynthesis*; D006900:Hydroxylation; D013302:Streptomyces / Q000254:growth & development / Q000378:metabolism*
D006894:Hydroxyestrones; D004970:Estrone