Amphomycin

Amphomycin is a lipopeptide antibiotic produced by Streptomycetes and Actinoplanes, initially isolated by researchers at Bristol-Myers in 1953 from Streptomyces canus. Amphomycin was marketed as a complex of closely related analogs in the 1950s and 1960s. Structure elucidation was not completed until 2000. Amphomycin is closely related to a number of "lost" antibiotics, aspartocin, crystallomycin, glumamycin, friulimicin, laspartocin, tsushimycin and zaomycin. Interest in Amphomycin was re-awakened with the discovery of friulimicin activity against antibiotic resistant strains. It can be studied as a scaffold for structural modifications.

Amphomycin is soluble in ethanol, methanol, DMF and DMSO.

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Background

Amphomycin inhibits peptidoglycan synthesis and blocks cell wall development. It inhibits peptidoglycan synthesis in both bacterial and mammalian systems, binding with phosphorylated substrates in a calcium-dependent way. Specifically, it blocks the transfer of phospho-N-acetylmuramyl pentapeptide form the UDP derivative to undecaprenylmonophosphate by interaction with dolichylmono-phosphate.