Biocatalyst mediated production of 6β,11α-dihydroxy derivatives of 4-ene-3-one steroids

• Efficient biotransformation of 4-ene-3-one steroids by using Mucor sp.
• Quantitative conversion of 4-ene-3-one steroids into 6β,11α-dihydroxy derivatives.
• Proposed biotransformation pathway for progesterone and testosterone by Mucor sp.
• Scale up studies for the production of 6β,11α-dihydroxy steroids using fermentor.
• Crystal structure of 6β,11α-dihydroxyprogesterone and 6β,11α-dihydroxytestosterone.

Biotransformation of steroids with 4-ene-3-one functionality such as progesterone (I), testosterone (II), 17α-methyltestosterone (III), 4-androstene-3,17-dione (IV) and 19-nortestosterone (V) were studied by using a fungal system belonging to the genera of Mucor (M881). The fungal system efficiently and quantitatively converted these steroids in regio- and stereo-selective manner into corresponding 6β,11α-dihydroxy compounds. Time course experiments suggested that the transformation was initiated by hydroxylation at 6β- or 11α-(10β-hydroxy in case of V) to form monohydroxy derivatives which upon prolonged incubation were converted into corresponding 6β,11α-dihydroxy derivatives. The fermentation studies carried out using 5 L table-top fermentor with substrates (I and II) clearly indicates that 6β,11α-dihydroxy derivatives of steroids with 4-ene-3-one functionality can be produced in large scale by using M881.

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