Microbiological synthesis of 16alpha, 18-dihydroxydeoxycorticosterone

16Alpha, 18-Dihydroxydeoxycorticosterone (16alpha, 18-dihydroxy-DOC) (1) and 1, 2-3H-16alpha, 18-dihydroxy-DOC (1,2-3H-16alpha, 18-dihydroxy-DOC) of high specific activity were obtained in good yield by microbiological hydroxylation of 18-OH-DOC and 1,2-3H-18-OH-DOC by Streptomyces roseochromogenus (ATCC 13400). The identity of the fermentation product to human adrenal produced 16alpha, 18-dihydroxy-DOC was established by chromatographic studies, derivative formation and gas-liquid chromatography. Yield of the product was about 30% of sutstrate and, allowing for losses in recovery, about 60% of the substrate 18-OH-DOC was converted to this product. A second product of fermentation isolated in lower yield appeared to be a dimer of 16alpha, 18-dihydroxy-DOC found in the acidic conditions of the fermentation. This method of synthesis of 16alpha, 18-dihydroxy-DOC is a practical way to make large quantities of the compound for further study of its possible role in human and experimental hypertension.