Synthesis of the Potassium Salt of 2,3,4,5-Tetrahydrodipicolinic Acid, a Key Intermediate in the Diaminopimelate Pathway to L-Lysine

Article abstract of DOI:10.1016/S0040-4039(00)79065-4

The potassium salt (13) of 2,3,4,5-tetrahydrodipicolinic acid, a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7), has been prepared by elimination of p-toluenesulphinic acid from the N-toluenesulphonyl derivative (12) of dimethyl cis-piperidine-2,6-dicarboxylate with simultaneous cleavage of the ester groups. 2,3,4,5-Tetrahydrodipicolinic acid exists in solution in equilibrium with the corresponding enamine (15) and an open chain form (14), and serves as a substrate for meso-DAP dehydrogenase on the biosynthetic pathway to L-lysine (7).Key Words: 2,3,4,5-Tetrahydrodipicolinic acid; diaminopimelate pathway; L-lysine biosynthesis; enzyme substrate; imine formation