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Biotransamination of Furan-Based Aldehydes with Isopropylamine: Enzyme Screening and pH Influence |
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| Authors: | Antía Pintor Nicoletta Cascelli Dr Alexey Volkov Prof Vicente Gotor-Fernández Prof Iván Lavandera |
| Affiliation: | 1. Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Spain
EnginZyme AB, Tomtebodavägen 6, 171 65 Solna, Sweden These authors contributed equally to this work.;2. Organic and Inorganic Chemistry Department, University of Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Spain;3. EnginZyme AB, Tomtebodavägen 6, 171 65 Solna, Sweden |
| Abstract: | Furan-based amines are highly valuable compounds which can be directly obtained via reductive amination from easily accessible furfural, 5-(hydroxymethyl)furfural (HMF) and 2,5-diformylfuran (DFF). Herein the biocatalytic amination of these carbonyl derivatives is disclosed using amine transaminases (ATAs) and isopropylamine (IPA) as amine donors. Among the different biocatalysts tested, the ones from Chromobacterium violaceum (Cv-TA), Arthrobacter citreus (ArS-TA), and variants from Arthrobacter sp. (ArRmut11-TA) and Vibrio fluvialis (Vf-mut-TA), afforded high levels of product formation (>80 %) at 100–200 mM aldehyde concentration. The transformations were studied in terms of enzyme and IPA loading. The pH influence was found as a key factor and attributed to the imine/aldehyde equilibrium that can arise from the high reactivity of the carbonyl substrates with a nucleophilic amine such as IPA. |
| Keywords: | amine transaminase furan-derived amines furfural 5-(hydroxymethyl)furfural isopropylamine |