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Cascade Coupling of Ene-Reductases and omega-Transaminases for the Stereoselective Synthesis of Diastereomerically Enriched Amines

Authors :
Monti, Daniela
Forchin, Maria Chiara
Crotti, Michele
Parmeggiani, Fabio
Gatti, Francesco G.
Brenna, Elisabetta
Riva, Sergio
Source :
ChemCatChem (Internet) 7 (2015): 3106–3109., info:cnr-pdr/source/autori:Monti, Daniela; Forchin, Maria Chiara; Crotti, Michele; Parmeggiani, Fabio; Gatti, Francesco G.; Brenna, Elisabetta; Riva, Sergio/titolo:Cascade Coupling of Ene-Reductases and omega-Transaminases for the Stereoselective Synthesis of Diastereomerically Enriched Amines/doi:/rivista:ChemCatChem (Internet)/anno:2015/pagina_da:3106/pagina_a:3109/intervallo_pagine:3106–3109/volume:7
Publication Year :
2015
Publisher :
Wiley-VCH, Weinheim , Germania, 2015.

Abstract

One-pot sequential and cascade processes performed by employing ene-reductases (ERs) together with -transaminases (-TAs) for the obtainment of diastereomerically enriched (R)- and (S)-amine derivatives containing an additional stereocenter were investigated. By using either - or -substituted unsaturated ketones as substrates and by coupling purified ERs belonging to the Old Yellow Enzyme (OYE) family with a panel of commercially available -TAs, the desired products were obtained in up to >99% conversion and >99%de. The sequential reactions were performed in a one-pot fashion with no need to adapt the reaction conditions to the reductive amination step or to purify the reaction intermediate. Moreover, high chemoselectivity of the tested -TAs for the saturated ketones was shown in the cascade reactions.

Details

Language :
English
Database :
OpenAIRE
Journal :
ChemCatChem (Internet) 7 (2015): 3106–3109., info:cnr-pdr/source/autori:Monti, Daniela; Forchin, Maria Chiara; Crotti, Michele; Parmeggiani, Fabio; Gatti, Francesco G.; Brenna, Elisabetta; Riva, Sergio/titolo:Cascade Coupling of Ene-Reductases and omega-Transaminases for the Stereoselective Synthesis of Diastereomerically Enriched Amines/doi:/rivista:ChemCatChem (Internet)/anno:2015/pagina_da:3106/pagina_a:3109/intervallo_pagine:3106–3109/volume:7
Accession number :
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