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.

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

Monti Daniela;Forchin Maria Chiara;Riva Sergio
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.
2015
Istituto di Chimica del Riconoscimento Molecolare - ICRM - Sede Milano
amines
biocatalysis
ene-reductases
stereoselectivity
transaminases
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Descrizione: Cascade Coupling of Ene-Reductases and omega-Transaminases for the Stereoselective Synthesis of Diastereomerically Enriched Amines
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/300062
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