Fungal platform for direct chiral phosphonic building blocks production. Closer look on conversion pathway.
The application of Rhodospirillum toruloides strain allowed resolving the chemically synthesized racemic mixtures of following chiral aminophosphonic acids: 1-aminoethylphosphonic acid (1), 1-amino-1-iso-propyl-1-phosphonic acid (2), 1-amino-1-phenylmethylphosphonic acid (4) and 1-amino-2-phenylethylphosphonic acid (3). The applied protocols resulted in obtaining pure (R)-1-aminoethylphosphonic acid (100 % of e.e.) and enantiomerically enriched mixtures of other phosphonates (73 % e.e. of (S)-1-amino-1-phenylmethylphosphonic acid, 51 % e.e. of (R)-1-amino-2-phenylethylphosphonic acid and 40 % e.e. of (S)-1-amino-2-methylpropylphosphonic acid). Products are valuable chiral building blocks and serve as aminophosphonic acids platform for further applications. Performed experiments allowed to define the path of xenobiotics bioconversion.
Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wybrzeże Wyspiańskiego 27, 50-370, Wrocław, Poland, ewa.zymanczyk-duda@pwr.edu.pl.
Ewa
E
Żymańczyk-Duda
Małgorzata
M
Brzezińska-Rodak
Kinga
K
Kozyra
Magdalena
M
Klimek-Ochab
D001487:Basidiomycota / Q000378:metabolism*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D063065:Organophosphonates