Baker’s yeasts driven synthesis of enantiomers of ethyl 1-hydroxy-1-(3,4-dimethoxyphenyl)methane(P-phenyl)phosphinate – Possible organophosphorus CDA’s

Add time:07/20/2019    Source:sciencedirect.com

Different forms of biocatalysts (baker’s yeasts) were applied for the kinetic resolution of ethyl ester of 1-hydroxy-1-(3,4-dimethoxyphenyl)-methane(P-phenyl)phosphinic acid via enantioselective oxidation of hydroxyl-functionality. Stereochemistry of the reaction was modulated by the bioconversion conditions (e.g. presence of defined chemical additives in the biotransformation medium) and by the use of different forms of the biocatalysts. The application of fresh baker’s yeasts (at the presence of sodium pyruvate in the reaction environment) resulted in the resolution of the enantiomeric pair RPS: SPR. Depending on the process conditions, both enantiomers were obtained with maximal yield and with the 100% of e.e. The second pair of enantiomers (SPS:RPR) was resolved with lyophilized baker’s yeast at the presence of methyl-vinyl ketone as chemical additive. This process allowed obtaining one of the enantiomers – RPR with 100% of e.e and with maximal yield.

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