Organic Chemistry: Current Research
Open Access

Abstract

Synthesis of Hydroxy-Androstane-1,4-Diene-3, 17-Dione Derivatives by Biotransformations of Bile Acids with Pseudomonas alcaliphila

Stefania Costa, Irene Rugiero, Elena Tamburini, Alessandro Medici, Giancarlo Fantin and Paola Pedrini

The synthesis of hydroxy-androstane-1,4-diene-3,17-dione derivatives (2a-d) by biotransformations with Pseudomonas alcaliphila of bile acids (1a-d) was reported. The scale-up of addition of deoxycholic acid (1a), cholic acid (1b), and chenodeoxycholic acid (1c) (1 g/L until 10 g/L) to the culture broth of P. alcaliphila switches the degradation process to the synthesis of 12β-hydroxy-androstane-1,4-diene-3,17-dione (2a, 95%), 7α,12β-dihydroxy-androstane- 1,4-diene-3,17-dione (2b, 52%), and 7α-hydroxy-androstane-1,4-diene-3,17-dione (2c, 23%) Also hyodeoxycholic acid (1d) was transformed by P. alcaliphila to 6α-hydroxy-androstane-1,4-diene-3,17-dione (2d) with as much good yields (83%) but with lower concentration (1 g/L) in the culture broth.