Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids

• Published in: Journal of molecular catalysis. B, Enzymatic Vol. 91; pp. 32 - 36
• Main Authors: Kozyra, Kinga, Brzezińska-Rodak, Małgorzata, Klimek-Ochab, Magdalena, Żymańczyk-Duda, Ewa
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.07.2013; Elsevier
• Subjects: Aspergillus niger; Aspergillus parasiticus; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; biotransformation; catalytic activity; Deracemization; enantiomers; Fundamental and applied biological sciences. Psychology; Fungi; Fusarium oxysporum; Methods. Procedures. Technologies; phosphorous acid; Talaromyces funiculosus; Whole-cell biocatalyst; α-Aminophosphonic acid; Fungi; Whole-cell biocatalyst; α-Aminophosphonic acid; Deracemization; Racemic; Biocatalysis; Separation; Enantiomer; Chiral compound; Biocatalyst
• ISSN: 1381-1177; 1873-3158
• DOI: 10.1016/j.molcatb.2013.02.004

[Display omitted] ► Fungal cells were applied to resolve racemic mixtures of α-aminophosphonic acids. ► This microbial transformation is considered as kinetically controlled bioconversion. ► The most potent appeared to be two different strains of Fusarium oxysporum. ► Optically pure enantiomers of ValP, PheP and PhgP were obtained. Several fungal species namely: Aspergillus niger, Aspergillus parasiticus, Penicillium funiculosum, Trigonopsis variabilis and two different strains of Fusarium oxysporum were tested toward racemic mixtures of following phosphonic acids: 1-amino-2-methylpropanephosphonic acid, 1-aminophenylmethanephosphonic acid and 1-amino-2-phenylethanephosphonic acid. Application of F. oxysporum strain (UW1) allowed obtaining optically pure S-isomer of 1-aminophenylmethanephosphonic acid and R-isomer of 1-amino-2-phenylethanephosphonic acid, whereas biotransformation of racemic mixture of 1-amino-2-methylpropanephosphonic acid with F. oxysporum strain (DSM 12646) cells resulted in obtaining pure enantiomer of R-configuration.