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.
| Mechanism of Action | 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. |
| Spectrum | Gram-positive bacteria |
| Plant Biology Applications | The effect of Amphomycin on the synthesis of polyprenyl-linked sugars and glycoproteins in plants was examined in vitro and in vivo. It blaocked the transfer of mannose form GDP-[14C]mannose into mannosyl-phos-phoryl-dolichol. It also inhibited the transfer of glucose form UDP-[14C]glucose to steryl glucosides, but this system was less sensitive to antibiotic than was synthesis of hte polyprenyl-linked sugars (Ericson et al, 1978). |
| Molecular Formula | C58H91N13O20 |
| References |
Aretz W et al (2000) Friulimicins: Novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. I. Taxonomic studies of the producing microorganism and fermentation. AJ. Antibiot. (Tokyo) 53(8):816-827 PMID 11079804 Ericson MC, GAfford JT and Elbein AD (1978) In vivo and in vitro inhibition of lipid-linked saccharide and glycoprotein synthesis in plants by Amphomycin. Arch. Biochem. Biophys. 191)2):698-704 Heineman B, Kaplan MA, Muir RD and Hooper IR (1953) Amphomycin. A new antibiotic. Antibiot. Chemother. (Northfield) 3(12):1239-1242 PMID 24542804 Tanaka H et al (1977) Studies on bacterial cell wall inhibitors. II. Inhibition of peptidoglycan synthesis in vivo and in vitro by Amphomycin. et al. Biochim. Biophys. Acta 497(3):633-640 Vertesy L et al (2000) Friulimicins: Novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. II. Isolation and structural characterization. 53(8):816-827 PMID 11079804 |