[bwana]

a beta dicarbonyl is used as a serine protease inhibitor where one of the carbonyls is an amide.  the alpha position between tthe two carbonyls are two fluorines rather than two hydrogens. i am struggling with how this molecule would interfere with the serine protease. it's an exercise in electron pushing that my brain has just given up on. can anyone give a little insight or point me to the right place where i can find some? tnx.

[sjb]

a beta dicarbonyl is used as a serine protease inhibitor where one of the carbonyls is an amide.  the alpha position between tthe two carbonyls are two fluorines rather than two hydrogens. i am struggling with how this molecule would interfere with the serine protease. it's an exercise in electron pushing that my brain has just given up on. can anyone give a little insight or point me to the right place where i can find some? tnx.

Consider tautomeric forms?

[Babcock_Hall]

Trifluormethylketones are strong serine protease inhibitors; the serine adds into the electrophilic carbonyl group and the result is something that mimics the first tetrahedral intermediate, with a negative charge on the oxygen atom.  Look for papers by Robert H. Abeles or Perry Frey in Biochemistry.  This is a little different from what you are describing, but a ketone that has two alpha fluorine atoms should still be fairly electrophilic, I suppose.