SKU: A005  / 
    CAS Number: 1402-82-0

    Amphomycin

    $209.00 - $729.00

    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