Highly Regioselective and Stereoselective Biohydroxylations of Oxandrolone

Paulina Łyczko,Alina Świzdor,Anna Panek

doi:10.3390/catal11010016

Abstract

Microbially catalyzed reactions are a powerful and valuable tool for organic synthesis of many compounds with potential biological activity. Herein, we report efficient hydroxylations of the steroidal anabolic-androgenic lactone, oxandrolone, in the cultures of three strains of fungi, Fusarium culmorum, Mortierella isabellina, and Laetiporus sulphureus. These reactions resulted in the production of four metabolites identified as 12β-hydroxyoxandrolone (2), 9α-hydroxyoxandrolone (3), 6α-hydroxyoxandrolone (4), and 15α-hydroxyoxandrolone (5), the latter being a new compound. The high substrate conversion rates and the product yields achieved indicate that these strains offer a new way to generate steroidal hydroxylactones with potential pharmaceutical interest. The structures of the isolated derivatives were characterized on the basis of spectroscopic data. The effect of modification of the A-ring structure of the steroid by the lactone group on the selectivity of hydroxylation in cultures of the tested fungi is also discussed.

Highlights

The ability of microorganisms to transform organic compounds makes them a suitable instrument for obtaining valuable molecules that cannot be formed by traditional chemical methods
Our results indicated that F. culmorum AM282, M. isabellina AM212 and L. sulphureu
Our were resultsable indicated that F.oxandrolone culmorum AM282, M. isabellina and L

Summary

Introduction

The ability of microorganisms to transform organic compounds makes them a suitable instrument for obtaining valuable molecules that cannot be formed by traditional chemical methods. As they occur at neutral pH and ambient temperature, and do not require expensive and harmful chemicals, biocatalytic reactions are easy to carry out, cost-effective and safe for the environment. The presence of a hydroxyl group in organic compounds affects their polarity, toxicity, extraction from the cell, and translocation via the cell membranes, while creating possibilities for various subsequent structural modifications in the search for new substances with healing properties [1,2].

Methods

Results

Conclusion