Total syntheses of bellenamine and its isomers.
The total synthesis of bellenamine was achieved by a modified CURTIUS procedure starting with D-beta-lysine. Bis(N-benzyloxycarbonyl)-D-beta-lysylglycine was converted to tris(N-benzyloxycarbonyl)bellenamine which was catalytically hydrogenated to yield bellenamine. D-beta-Lysine was synthesized from D-ornithine by the ARNDT-EISTERT homologation sequence. Three isomers, L-beta-lysyl, D- and L-lysyl congeners synthesized by a similar method, showed no antibacterial activities.
Ikeda
Y
Y
Institute of Microbial Chemistry, Tokyo, Japan.
Ikeda
D
D
Kondo
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008239:Lysine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000737:chemistry
D000900:Anti-Bacterial Agents; C048662:beta-lysylmethanediamine; D008239:Lysine