An antibacterial lipopeptide
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Amphomycin

Item No. 17091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2'-((6S,9R,15S,21S,24S,26aR,33S,34R,36aS)-9-((R)-1-aminoethyl)-33-((2S)-3-carboxy-2-((Z)-10-methyldodec-3-enamido)propanamido)-24-((S)-1-carboxyethyl)-6-isopropyl-34-methyl-5,8,11,14,17,20,23,26,32,36-decaoxotetratriacontahydro-1H,5H-pyrido[1,2-a]pyrrolo[1,2-y][1,4,7,10,13,16,19,22,25,28]decaazacyclohentriacontine-15,21-diyl)diacetic acid
CAS Number
1402-82-0
Molecular Formula
C58H91N13O20
Formula Weight
1290.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C([C@@H]1N(CCCC1)C([C@@](NC([C@@H](NC(C/C=C\CCCCCC(CC)C)=O)CC(O)=O)=O)([C@H](NC([C@@H]2CCCN2C([C@@H](NC([C@@]([H])([C@H](N)C)N3)=O)C(C)C)=O)=O)C)[H])=O)N[C@@]([C@@H](C(O)=O)C)(C(N[C@H](C(NCC(N[C@@H](CC(O)=O)C(NCC3=O)=O)=O)=O)CC(O)=O)=O)[H]
InChi Code
InChI=1S/C58H91N13O20/c1-8-30(4)18-13-11-9-10-12-14-21-39(72)63-36(26-44(79)80)51(83)69-48-33(7)62-52(84)38-20-17-23-71(38)56(88)45(29(2)3)67-55(87)47(32(6)59)66-41(74)28-61-49(81)34(24-42(75)76)64-40(73)27-60-50(82)35(25-43(77)78)65-54(86)46(31(5)58
InChi Key
WAFOSUDOWLQGBG-NUZIGYSUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $347

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    5 mg

    $1,040

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    Cayman Chemical
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    Product Description

    Amphomycin is a natural antibacterial lipopeptide first isolated from S. canus. Lipopeptides are cyclic depsipeptides with a peptidyl side chain capped with a saturated alkyl tail.1 They preferentially target Gram-positive bacteria and may be useful against drug resistant strains.1 Amphomycin is also an inhibitor of peptidoglycan synthesis in both bacterial and mammalian systems, as it binds with phosphorylated substrates in a calcium-dependent manner.2,3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fair, R.J., and Tor, Y. Antibiotics and bacterial resistance in the 21st century. Perspect. Medicin. Chem. 6, 25-64 (2014).

    2. Spencer, J.P., and Elbein, A.D. Transfer of mannose from GDP-mannose to lipid-linked oligosaccharide by soluble mannosyl transferase. Proc. Natl. Acad. Sci. USA 77(5), 2524-2527 (1980).

    3. Kang, M.S., Spencer, J.P., and Elbein, A.D. Amphomycin inhibition of mannose and GlcNAc incorporation into lipid-linked saccharides. The Journal of Biological Chemisty 253(24), 8860-8866 (1978).

    4. Banerjee, D.K. Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. The Journal of Biological Chemisty 264(4), 2024-2028 (1989).

    5. Cooper, H.N., Gurcha, S.S., Nigou, J., et al. Characterization of mycobacterial protein glycosyltransferase activity using synthetic peptide acceptors in a cell-free assay. Glycobiology 12(7), 427-434 (2002).