Complete Epoxy Phosphonate Conversion to Dimethyl (1E)-3-hydroxyprop-1-enylphosphonate with Photobiocatalysts’ Assistance

Phosphonates derivatives are compounds of interests and are applied as drugs of e.g. antibacterial antiviral activities, what is connected with their inhibitory activity towards different enzymes, what in turn is in the relation to the configuration of particular compounds izomers. Biological synthesis of such molecules is the method of choice and can be carried on with enzymes or whole cells of organisms. Photobiocatalysts employed in bioconversion of epoxy dimethyl phosphonate are able to convert this substrate into geometric isomers of the unsaturated product, which is classified as very rare and expensive compound of high added value. Six different strains were screened towards dimethyl epoxy phosphonate and in case of Synechococcus bigranulatus 99% of conversion degree was achieved. Product structure and yield of the reaction were confirmed with Mass Spectroscopy (MS); Nuclear Magnetic Resonance (NMR) of isotopes 1H, 13C, and 31P, 2D NMR; and Infrared Spectroscopy (IR).