Diethyl [2,2,2-trifluoro-1-phenyl­sulfonyl­amino-1-(trifluoro­meth­yl)eth­yl]phospho­nate
2008

Study of a New Compound for Inhibiting Enzymes

publication Evidence: moderate

Author Information

Author(s): Wijeyesakere Sanjeeva J., Nasser Faik A., Kampf Jeff W., Aksinenko Alexey Y., Sokolov Vladimir B., Malygin Vladimir V., Makhaeva Galina F., Richardson Rudy J.

Primary Institution: University of Michigan

Hypothesis

Inhibition of serine hydrolases by FAP compounds occurs via scission of the P—C bond to organophosphorylate the active site serine.

Conclusion

The structure of diethyl-FAP revealed an elongated P—C bond that is expected to be labile, explaining its ability to inhibit serine hydrolases.

Supporting Evidence

  • The compound's structure contains a P—C bond and two intermolecular hydrogen bonds, forming dimers.
  • The elongated P—C bond in diethyl-FAP is similar to that in diisopentyl-FAP, suggesting similar reactivity.
  • The study indicates that certain enzymes can break down stable P—C bonds, which could help in environmental cleanup.

Takeaway

Scientists created a new chemical compound that can stop certain enzymes from working, which could help in cleaning up harmful substances in the environment.

Methodology

The compound was synthesized by mixing diethylphosphite and the sulfonylimine of hexafluoroacetone, followed by recrystallization.

Digital Object Identifier (DOI)

10.1107/S1600536808020175

Want to read the original?

Access the complete publication on the publisher's website

View Original Publication