Use of Immobilized Amine Transaminase from Vibrio fluvialis under Flow Conditions for the Synthesis of (S)‐1‐(5‐Fluoropyrimidin‐2‐yl)‐ethanamine
- Riccardo Semproli [a]
- Gianmarco Vaccaro [a],[b]
- Erica E. Ferrandi [c]
- Marta Vanoni [c]
- Teodora Bavaro [a]
- Giorgio Marrubini [a]
- Francesca Annunziata [b]
- Paola Conti [b]
- Giovanna Speranza [d]
- Daniela Monti [*c]
- Lucia Tamborini [*b]
- Daniela Ubiali [*a]
- [a] R. Semproli, G. Vaccaro, Dr. G. Marrubini, Dr. T. Bavaro, Prof. D. Ubiali, Department of Drug Sciences, University of Pavia, Viale Taramelli 12, I-27100 Pavia, Italy
- [b] G. Vaccaro, F. Annunziata, Prof. P. Conti, Prof. L. Tamborini, Department of Pharmaceutical Sciences, University of Milano, Via Mangiagalli 25, I-20133 Milano, Italy
- [c] Dr. E. E. Ferrandi, M. Vanoni, Dr. D. Monti, Istituto di Scienze e Tecnologie Chimiche "Giulio Natta" (SCITEC) – CNR, Via Bianco 9, I-20131 Milano, Italy
- [d] Prof. G. Speranza, Department of Chemistry, University of Milano, Via Golgi 19, I-20133 Milano, Italy
Read the publication that featured this abstractWe report on the covalent immobilization of the (S)‐selective amine transaminase from Vibrio fluvialis (Vf‐ATA) and its use in the synthesis of (S)‐1‐(5‐fluoropyrimidin‐2‐yl)‐ethanamine, a key intermediate of the JAK2 kinase inhibitor AZD1480. Immobilized Vf‐ATA on glyoxyl‐agarose (activity recovery: 30%) was used in a packed bed reactor to set‐up a continuous flow biotransformation coupled with a straightforward in‐line purification to circumvent the 2‐step process described in literature for the batch reaction. The newly developed biotransformation was run in a homogeneous system including dimethyl carbonate as a green co‐solvent. Optically pure (S)‐1‐(5‐fluoropyrimidin‐2‐yl)‐ethanamine (ee >99%) was isolated in 35% yield.
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