title: Biocatalytic functionalization of hydroxyalkyl acrylates and phenoxyethanol via phosphorylation.
abstract: 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).
authors.affiliation: Austrian Centre of Industrial Biotechnology, c/o; Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.
authors.forename: Gábor
authors.initials: G
authors.lastname: Tasnádi
authors.affiliation: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.
authors.forename: Mélanie
authors.initials: M
authors.lastname: Hall
authors.affiliation: White Biotechnology Research Biocatalysis, BASF SE, Carl-Bosch-Strasse 38, 67056 Ludwigshafen, Germany.
authors.forename: Kai
authors.initials: K
authors.lastname: Baldenius
authors.affiliation: White Biotechnology Research Biocatalysis, BASF SE, Carl-Bosch-Strasse 38, 67056 Ludwigshafen, Germany.
authors.forename: Klaus
authors.initials: K
authors.lastname: Ditrich
authors.affiliation: Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria. Electronic address: Kurt.Faber@Uni-Graz.at.
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
mesh_terms: D000135:Acid Phosphatase / Q000378:metabolism*; D000179:Acrylates / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D019149:Bioreactors; D004800:Enzymes, Immobilized / Q000378:metabolism*; D005026:Ethylene Glycols / Q000737:chemistry / Q000378:metabolism*; D010766:Phosphorylation
chemical_list: D000179:Acrylates; D004800:Enzymes, Immobilized; D005026:Ethylene Glycols; D000135:Acid Phosphatase; C005398:phenoxyethanol
keywords: Biocatalysis; Continuous flow system; Kinetic control; Phosphatase; Phosphorylation; Reaction engineering