A high yielding bioprocess for 11-α hydroxylation of canrenone (1a) using Aspergillus ochraceus ATCC 18500 was developed. The optimization of the biotransformation involved both fermentation (for achieving highly active mycelium of A. ochraceus) and biotransformation with the aim to obtain 11-α hydroxylation with high selectivity and yield. A medium based on sucrose as C-source resulted particularly suitable for conversion of canrenone into the corresponding 11-hydroxy derivative, whereas the use of O2-enriched air and dimethyl sulfoxide (DMSO) as a co-solvent for increasing substrate solubility played a crucial role for obtaining high yields (>95%) of the desired product in high chemical purity starting from 30 mM (10.2 g/L) of substrate. The structure of the hydroxylated product was confirmed by a combination of two-dimensional NMR proton-proton correlation techniques.

Development of a high-yielding bioprocess for 11-α hydroxylation of canrenone under conditions of oxygen-enriched air supply / M.L. Contente, B. Guidi, I. Serra, V. De Vitis, D. Romano, A. Pinto, R. Lenna, R.P. de Souza Oliveira, F. Molinari. - In: STEROIDS. - ISSN 0039-128X. - 116(2016 Dec), pp. 1-4. [10.1016/j.steroids.2016.09.013]

Development of a high-yielding bioprocess for 11-α hydroxylation of canrenone under conditions of oxygen-enriched air supply

M.L. Contente;B. Guidi;I. Serra;V. De Vitis;D. Romano;A. Pinto;F. Molinari
2016-12

Abstract

A high yielding bioprocess for 11-α hydroxylation of canrenone (1a) using Aspergillus ochraceus ATCC 18500 was developed. The optimization of the biotransformation involved both fermentation (for achieving highly active mycelium of A. ochraceus) and biotransformation with the aim to obtain 11-α hydroxylation with high selectivity and yield. A medium based on sucrose as C-source resulted particularly suitable for conversion of canrenone into the corresponding 11-hydroxy derivative, whereas the use of O2-enriched air and dimethyl sulfoxide (DMSO) as a co-solvent for increasing substrate solubility played a crucial role for obtaining high yields (>95%) of the desired product in high chemical purity starting from 30 mM (10.2 g/L) of substrate. The structure of the hydroxylated product was confirmed by a combination of two-dimensional NMR proton-proton correlation techniques.
Aspergillus ochraceus; Biocatalysis; Biotransformation; Canrenone; Monooxygenase; Steroid hydroxylation; Biochemistry; Molecular Biology; Pharmacology; Endocrinology; Clinical Biochemistry; Organic Chemistry
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Settore CHIM/10 - Chimica degli Alimenti
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/444297
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