Effective fungal catalyzed synthesis of P-chiral organophosphorus compounds

Application of the Beauveria bassiana Strain for the Enantioselective Oxidation of the Diethyl 1-Hydroxy-1-Phenylmethanephosphonate

“…This work was inspired by our previous studies [ 3 , 23 ], which employed different strains of fungi for the synthesis of P-chiral hydroxyphosphonate via enantioselective oxidation of hydroxyl functionality. Chemical procedures of the synthesis as well as prochiral keto phosphonates and racemic hydroxylphosphonates are cheap and efficient, therefore, these compounds can serve as convenient substrates for further reactions, including the biocatalyzed synthesis of the chiral products in a manner as simple and as economic as possible.…”

“…They act as antibacterials, antivirals, neuromodulators, chelating agents in bone diseases or herbicides, and also they can serve as chiral building blocks in combinatorial chemistry [ 2 , 4 – 6 , 12 ]. Biocatalyzed synthesis of chiral, organophosphorus compounds is still not fully explored, although during last decade purified enzymes and whole microbial cells were successfully used for the synthesis of structurally different, optically pure phosphonate derivatives [ 3 , 8 , 10 , 11 , 15 , 19 , 21 , 22 , 24 ]. Here, we report effective and simple strategy, which allowed obtaining non-racemic, diethyl 1-hydroxy-1-phenylmethanephosphonate in both optical forms, with the yield of 20% (resolution of the racemic mixtures is under kinetic control) (Fig.…”

Biocatalytic Resolution of Enantiomeric Mixtures of 1-Aminoethanephosphonic Acid

“…In previous works we have employed various strains of fungi for the synthesis of P-chiral hydroxyphosphonates [ 21 ] and for the oxidative resolution of racemic mixtures of diethyl 1-hydroxy-phenylmethanephosphonate [ 39 ]. The success of these reactions was an inspiration for the use of whole cells of microorganisms for the resolution of racemic mixtures of 1-aminoethanephosphonic acid.…”

“…The biocatalytic resolution of racemic molecules has attracted the interest of chemists for several decades [ 17 , 18 , 19 , 20 ]. Microbial biocatalysts in the form of purified enzymes or whole microbial cells have been successfully used for synthesis of optically pure organophosphonate derivatives [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ], showing the utility of biocatalysis in this branch of chemistry. Surprisingly, bioconversion is scarcely used to obtain optically pure aminophosphonic compounds [ 30 , 31 , 32 , 33 , 34 , 35 ].…”

Research paper Microbial biotransformation of two phosphonoacetic acid derivatives bearing two stereomeric centres

“…Kinetic resolution of enantiomers of ethyl hydroxy(phenyl)methane(P -phenyl) phosphinate (a compound with two stereogenic centres but without the carboxylic group) has been tested earlier, using several bacterial strains . Enantioselective biooxidation by fungi of ethyl hydroxy(phenyl)-methane(P -phenyl) phosphinate has also been previously investigated (Klimek-Ochab et al, 2008).…”