Equation Presented Vinylogous amides 5 and 6 have been synthesized from L-propargyl glycine and tested against diaminopimelate (DAP) enzymes involved in bacterial lysine biosynthesis. Both are reversible inhibitors of DAP D-dehydrogenase and DAP epimerase with IC50 values in the 500 μM range. Compound 5 shows competitive inhibition against the L-dihydrodipicolinate (DHDP) reductase with a Ki value of 32 μM, which is comparable to the planar dipicolinate 16 (Ki = 26 μM), the best known inhibitor of the enzyme.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry