One-pot sequential and cascade processes performed by employing ene-reductases (ERs) together with omega- transaminases (w-TAs) for the obtainment of diastereomerically enriched (R)- and (S)-amine derivs. contg. an addnl. stereocenter were investigated. By using either alpha- or beta-substituted unsatd. ketones as substrates and by coupling purified ERs belonging to the Old Yellow Enzyme (OYE) family with a panel of com. available w-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 w-TAs for the satd. ketones was shown in the cascade reactions. ~

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

CROTTI, MICHELE;PARMEGGIANI, FABIO;GATTI, FRANCESCO GILBERTO;BRENNA, MARIA ELISABETTA;
2015-01-01

Abstract

One-pot sequential and cascade processes performed by employing ene-reductases (ERs) together with omega- transaminases (w-TAs) for the obtainment of diastereomerically enriched (R)- and (S)-amine derivs. contg. an addnl. stereocenter were investigated. By using either alpha- or beta-substituted unsatd. ketones as substrates and by coupling purified ERs belonging to the Old Yellow Enzyme (OYE) family with a panel of com. available w-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 w-TAs for the satd. ketones was shown in the cascade reactions. ~
2015
File in questo prodotto:
File Dimensione Formato  
cctc.201500424.pdf

Accesso riservato

Descrizione: Finale
: Publisher’s version
Dimensione 442.29 kB
Formato Adobe PDF
442.29 kB Adobe PDF   Visualizza/Apri
ER-TAper vqr.pdf

accesso aperto

Descrizione: pre-print
: Pre-Print (o Pre-Refereeing)
Dimensione 594.34 kB
Formato Adobe PDF
594.34 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/969818
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 37
  • ???jsp.display-item.citation.isi??? 33
social impact