16α-Hydroxy Steroids. XII.^1a 21-Amino Derivatives of 9α-Fluorohydrocortisone

16α-Hydroxysteroids. XIII.* Carbonyl Reduction by Streptomyces roseochromogenus

“…The characteristic pattern of unaltered tetrao!, 16a-monoacetate, 21-monoacetate, and 16a,21diacetate (in increasing order of chromatographic mobility), becomes a very specific means of recognition of such steroids. the aldehyde IV does not appear to be a biological intermediate in the formation of 21-acetylamino-9 -fluoro -11,3,17 -dihydroxy -4 -pregnene-3,20-dione from I by S. roseochromogenus (Smith et al, 1962). The aldehyde IV is not hydroxylated by S. roseochromogenus; neither 16 a-nor 2/3hydroxylated derivatives could be detected.3 Experimental 9a-Fluoro-l 1ß,17 a,203,21 -tetrahydroxy-4-pregnen-3-one (II).-The steroid-rich broth extract concentrate obtained from S. roseochromogenus fermentations of 9a-fluorohydrocortisone already described (Smith et al, 1961) was used for the isolation of 20/3-dihydro-9a-fluorohydrocortisone.…”

“…In our studies of the 16 -hydroxy latió n of 9afluorohydrocortisone (I) by Streptomyces roseochromogenus a variety of reducing (Smith et al, 1960b;Smith et al, 1961) and non-reducing (Smith et al, 1962) steroids have been isolated and identified.…”

“…Only the most mobile and the least mobile zones were examined. From the RF 0.4 zone (after elution and rechromatography) 21-acetylamino-9a-fluoro-ll/3, 17a -dihydroxy -4 -pregnene -3,20 -dione (Smith et al, 1962) was isolated.…”