Synthesis and antimicrobial activity of sperabillin derivatives.
Modification of sperabillins was carried out. The 2-amidinoethylamino moiety was removed by brief acidic hydrolysis. The 2,4-hexadienoyl moiety was hydrogenated to the hexanoyl moiety and this was cleaved by an enzymatic reaction using the cells of Pseudomonas acidovorans IFO 13582. The 2-amidinoethylamino and the 2,4-hexadienoyl moieties were replaced with other groups. The derivative which was prepared by condensation of two molar amounts of dehexadienoylsperabillin A with (E,E)-muconic acid showed better protective effects than sperabillin A against Gram-negative bacteria.
Hida
T
T
Discovery Research Laboratories II, Osaka, Japan.
Tsubotani
S
S
Katayama
N
N
Funabashi
Y
Y
Natsugari
H
H
Harada
S
S
D000578:Amidines / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007928:Lethal Dose 50; D051379:Mice; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D000578:Amidines; D000900:Anti-Bacterial Agents; C073531:sperabillin C; C073530:sperabillin B; C073529:sperabillin A; C073532:sperabillin D