Tetrahedron p. 10241 - 10252 (1995)
Update date:2022-08-11
Topics:
Chrystal, Ewan J. T.
Couper, Lynda
Robins, David J.
2,3,4,5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesulfinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis-piperidine-2,6-dicarboxylate with concomitant cleavage of the esther groups. (±)-2,3,4,5-Tetrahydrodipicolinic acid is unstable in neutral or acidic solution, and in basic solution it exists in equilibrium with the corresponding enamine (27) and 2-oxo-6-aminoadipate (26).
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