L-glutamic acid diketopiperazine omega-alkenyl esters were synthesized and polymerized via acyclic diene metathesis polycondensation chemistry using ruthenium catalysts. The polycondensation of L-glutamic acid diketopiperazine omega-allyl ester (1) was unsuccessful, while the polycondensation Of L-glutamic acid diketopiperazine omega-homoallyl ester (2), -pentenyl ester (3), and -hexenyl ester (4) with Grubbs second-generation catalyst and Grubbs-Hoveyda catalyst satisfactorily proceeded to give the corresponding polymers. They exhibited melting temperatures around 150 degrees C, and possessed crystalline structures similar to that of polyethylene. Dynamic light scattering and differential scanning calorimetric measurements suggested that the polymers formed aggregates in N,N-dimethylformamide, presumably based on hydrogen bonding between diketopiperazine moieties.