Biocatalytic functionalization of hydroxyalkyl acrylates and phenoxyethanol via phosphorylation.

Autor: Tasnádi G; Austrian Centre of Industrial Biotechnology, c/o; Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria., Hall M; Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria., Baldenius K; White Biotechnology Research Biocatalysis, BASF SE, Carl-Bosch-Strasse 38, 67056 Ludwigshafen, Germany., Ditrich K; White Biotechnology Research Biocatalysis, BASF SE, Carl-Bosch-Strasse 38, 67056 Ludwigshafen, Germany., Faber K; Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria. Electronic address: Kurt.Faber@Uni-Graz.at.
Jazyk: angličtina
Zdroj: Journal of biotechnology [J Biotechnol] 2016 Sep 10; Vol. 233, pp. 219-27. Date of Electronic Publication: 2016 Jul 12.
DOI: 10.1016/j.jbiotec.2016.07.009
Abstrakt: The enzymatic phosphorylation of phenoxyethanol, 2-hydroxyethyl acrylate and 4-hydroxybutyl acrylate catalyzed by acid phosphatases PhoN-Sf and PiACP at the expense of inorganic di-, tri-, hexameta- or polyphosphate was applied to the preparative-scale synthesis of phosphorylated compounds. The reaction conditions were optimized with respect to enzyme immobilization, substrate concentration, pH and type of phosphate donor. The mild reaction conditions prevented undesired polymerization and hydrolysis of the acrylate ester moiety. Application of a continuous flow system allowed facile scale-up and mono-phosphates were obtained in up to 26% isolated yield with space-time yields of 0.89kgL(-1)h(-1).
(Copyright © 2016 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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