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Use of Immobilized Amine Transaminase from Vibrio fluvialis under Flow Conditions for the Synthesis of ( S )‐1‐(5‐Fluoropyrimidin‐2‐yl)‐ethanamine
Author(s) -
Semproli Riccardo,
Vaccaro Gianmarco,
Ferrandi Erica E.,
Vai Marta,
Bavaro Teodora,
Marrubini Giorgio,
Annunziata Francesca,
Conti Paola,
Speranza Giovanna,
Monti Daniela,
Tamborini Lucia,
Ubiali Daniela
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201902080
Subject(s) - biotransformation , chemistry , flow chemistry , amine gas treating , biocatalysis , yield (engineering) , green chemistry , combinatorial chemistry , organic chemistry , catalysis , chromatography , enzyme , reaction mechanism , materials science , metallurgy
We 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.