PMID:11101437
| Citation |
Caplan, JF, Zheng, R, Blanchard, JS and Vederas, JC (2000) Vinylogous amide analogues of diaminopimelic acid (DAP) as inhibitors of enzymes involved in bacterial lysine biosynthesis. Org. Lett. 2:3857-60 |
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| Abstract |
[reaction: see text] 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 IC(50) values in the 500 microM range. Compound 5 shows competitive inhibition against the L-dihydrodipicolinate (DHDP) reductase with a K(i) value of 32 microM, which is comparable to the planar dipicolinate 16 (K(i) = 26 microM), the best known inhibitor of the enzyme. |
| Links | |
| Keywords |
Amides/chemical synthesis; Amides/chemistry; Amino Acid Isomerases/antagonists & inhibitors; Amino Acid Oxidoreductases/antagonists & inhibitors; Anti-Bacterial Agents/chemical synthesis; Anti-Bacterial Agents/chemistry; Bacteria/chemistry; Bacteria/metabolism; Diaminopimelic Acid/analogs & derivatives; Diaminopimelic Acid/chemical synthesis; Diaminopimelic Acid/chemistry; Dihydrodipicolinate Reductase; Enzyme Inhibitors/chemical synthesis; Enzyme Inhibitors/chemistry; Lysine/biosynthesis; Oxidoreductases/antagonists & inhibitors; Oxidoreductases Acting on CH-CH Group Donors |
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