A pyridoxal 5'-phosphate-dependent transaminase (ATA-117) was selected and covalently immobilized on Eupergit®C to enhance its operational stability and reusability. A stereoselective transamination, followed by a spontaneous intramolecular aza-Michael reaction, was performed to synthesize natural (- )-pinidinone (10.1021/jacs.6b07024). The reaction was then optimized in a continuous flow system evaluating substrate concentration, isopropylamine equivalents, reaction temperature, residence time, type and amount of cosolvent.
From Batch to Flow: Chemo-Enzymatic Asymmetric Synthesis of Piperidine Scaffolds / S. Vicinanza, S. Patti, M. Pirotta, I. Magrini Alunno, F. Annunziata, R. Gandolfi, C. Borsari, I. Bassanini, D. Monti, E. Elisa Ferrandi, L. Tamborini. 39. New Trends in Organic Synthesis : November, 24 Milano 2025.
From Batch to Flow: Chemo-Enzymatic Asymmetric Synthesis of Piperidine Scaffolds
S. VicinanzaPrimo
;S. PattiSecondo
;F. Annunziata;R. Gandolfi;C. Borsari;I. Bassanini;L. TamboriniUltimo
2025
Abstract
A pyridoxal 5'-phosphate-dependent transaminase (ATA-117) was selected and covalently immobilized on Eupergit®C to enhance its operational stability and reusability. A stereoselective transamination, followed by a spontaneous intramolecular aza-Michael reaction, was performed to synthesize natural (- )-pinidinone (10.1021/jacs.6b07024). The reaction was then optimized in a continuous flow system evaluating substrate concentration, isopropylamine equivalents, reaction temperature, residence time, type and amount of cosolvent.
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