title: Lipases and whole cell biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and its ester.
abstract: A wide spectrum of commercially available lipases and microbial whole cells catalysts were tested for biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid 1 and its butyryl ester. The best results were achieved for biocatalytic hydrolysis of ester: 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid 2 performed by lipase from Candida cylindracea, what gave optically active products with 85% enantiomeric excess, 50% conversion degree and enantioselectivity 32.9 for one pair of enantiomers. Also enzymatic systems of Penicillium minioluteum and Fusarium oxysporum were able to hydrolyze tested compound with high enantiomeric excess (68-93% ee), enantioselectivity (44 for one pair of enantiomers) and conversion degree about 50-55%. Enzymatic acylation of hydroxyphosphinate was successful in case when porcine pancreas lipase was used. After 4days of biotransformation the conversion reaches 45% but the enantiomeric enrichment of the isomers mixture do not exceed 43%. Obtained chiral compounds are valuable derivatizing agents for spectroscopic (NMR) evaluation of enantiomeric excess for particular compounds (e.g. amino acids).
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland. Electronic address: paulina.majewska@pwr.edu.pl.
authors.forename: Paulina
authors.initials: P
authors.lastname: Majewska
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Monika
authors.initials: M
authors.lastname: Serafin
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Magdalena
authors.initials: M
authors.lastname: Klimek-Ochab
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Brzezińska-Rodak
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Ewa
authors.initials: E
authors.lastname: Żymańczyk-Duda
mesh_terms: D001711:Biotransformation; D004952:Esters / Q000737:chemistry / Q000378:metabolism*; D005658:Fungi / Q000166:cytology / Q000378:metabolism*; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D010721:Phosphinic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*
chemical_list: D004952:Esters; D010721:Phosphinic Acids; D008049:Lipase
keywords: Biocatalysis; Hydroxyphosphonates; Lipolytic activity