Attempts at the enzymatic synthesis of chiral ester derivatives of 1,3,5-triaza-7-phosphaadamantane (PTA)

Abstract

The enzyme-promoted hydrolysis of racemic ester derivatives of PTA 11 and its P-sulfide 12 gave unreacted esters and corresponding acids, which were converted into ester, in moderate yield depending on the solvent and enzyme applied. However, in all cases the products were racemic mixtures.

Graphical Abstract

Keywords:

• 1,3,5-Triaza-7-phosphaadamantane (PTA)
• ester derivative of PTA
• P-sulfide ester derivative of PTA
• kinetic resolution
• hydrolysis

Acknowledgements

The authors thank to prof. R. Ostaszewski for a generous gift of liver acetone powders.

Conflicts of interest

The authors declare no conflict of interest.

Additional information

Funding

The project was financed from European Union with European Regional Development Fund, Foundation for Polish Science, Grant for Innovation upon Operational Programme—Innovative Economy, Priority 1: Research and development for new technologies, Measure 1.2: Improvement of the human potential of science; Parent Bridge Programme POMOST/2013-8/9 (for M.K.).