Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid

meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of l-lysine has been prepared differentially protected in a stereospecific manner from both l-aspartic and l-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane®. S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate.