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First attempts at the enzyme-promoted hydrolysis of N-acyl phosphonoamides

Piotr Kiełbasiński 1Małgorzata Kwiatkowska 1Adam Redzej 2Ryszard Ostaszewski 2

1. Polish Academy of Sciences, Center of Molecular and Macromolecular Studies (CMMS-PAS), Sienkiewicza 112, Łódź 90-363, Poland
2. Polish Academy of Science, Institute of Organic Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland


P-Chiral organophosphorus compounds play an important role both in mechanistic studies and as biologically active species. Among a variety of methods of their synthesis those based on enzyme-mediated transformations have recently become a valuable supplement [1]. Continuing our earlier works on the application of hydrolytic enzymes in the synthesis of functionalized chiral organophosphorus derivatives [2], we became interested in using this methodology in the synthesis of P-chiral non-racemic phosphonoamides, the compounds which are difficult to obtain via traditional chemical methods. To achieve this, we screened a series of hydrolytic enzymes for the stereoselective hydrolysis of a variety of N-acyl phosphonoamides under kinetic resolution conditions.


Although a number of enzymes proved unreactive towards particular substrates, some of them were found to catalyze the desired reaction. The influence of the substituents at phosphorus and the kind of enzyme on the reaction outcome will be discussed.


This work was supported by the network "Synthesis, Structure and Therapeutic Properties of Compounds and Organic Substances".

[1] P. Kiełbasiński, M. Mikołajczyk, "Chiral heteroatom-containing compounds” in Future Directions in Biocatalysis, T. Matsuda (Ed.), Elsevier, Amsterdam 2007, pp.159-203.
[2] P. Kiełbasiński, M. Rachwalski, M. Mikołajczyk, F. P. J. T. Rutjes, Tetrahedron: Asymmetry 2008, 19, 562-567 and references therein.


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    Submitted: 2008-03-12 23:15
    Revised:   2009-06-07 00:48