Ethyl secodione (1) has been enantioselectively reduced by using different biocatalysts for the preparation of ethyl secol (13R, 17S)-2a. The recombinant ketoreductase KRED1-Pglu converted the substrate with the highest reaction rate and stereoselectivity (ee > 98 %), whereas whole cells of Pichia minuta CBS 1708 showed the highest productivity. Stereoselective reduction of 1 provides the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene). Recombinant ketoreductase KRED1-Pglu and whole cells of yeasts provide the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene) with excellent stereoselectivity.

Contente, M., Molinari, F., Serra, I., Pinto, A., Romano, D. (2016). Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(7), 1260-1263 [10.1002/ejoc.201501557].

Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids

Serra I.;
2016

Abstract

Ethyl secodione (1) has been enantioselectively reduced by using different biocatalysts for the preparation of ethyl secol (13R, 17S)-2a. The recombinant ketoreductase KRED1-Pglu converted the substrate with the highest reaction rate and stereoselectivity (ee > 98 %), whereas whole cells of Pichia minuta CBS 1708 showed the highest productivity. Stereoselective reduction of 1 provides the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene). Recombinant ketoreductase KRED1-Pglu and whole cells of yeasts provide the key chiral precursor for the synthesis of a number of hormonal contraceptives (i.e., desogestrel, norgestrel, gestodene) with excellent stereoselectivity.
Articolo in rivista - Articolo scientifico
Enzymatic reduction; Enzymes; Hormones; Steroids; Yeast;
English
2016
2016
7
1260
1263
none
Contente, M., Molinari, F., Serra, I., Pinto, A., Romano, D. (2016). Stereoselective Enzymatic Reduction of Ethyl Secodione: Preparation of a Key Intermediate for the Total Synthesis of Steroids. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016(7), 1260-1263 [10.1002/ejoc.201501557].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/316417
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