A depsipeptide antibiotic
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Enopeptin A

Item No. 17092

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R)-N-[(2E,4E,6E,8E,10E)-12-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-1,12-dioxo-2,4,6,8,10-dodecapentaen-1-yl]-L-phenylalanyl-L-seryl-L-prolyl-L-proline, (6→2)-lactone
CAS Number
139601-96-0
Synonyms
  • BRN 537924
  • NSC 657143
Molecular Formula
C47H57N7O11
Formula Weight
896.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](COC2=O)C(N3[C@H](C(N([C@@H](C)C(N[C@H](C(N4[C@H]2C[C@@H](C)C4)=O)C)=O)C)=O)CCC3)=O)=O)/C=C/C=C/C=C/C=C/C=C/C(NC5=C(O)CCC5=O)=O
InChi Code
InChI=1S/C47H57N7O11/c1-29-25-36-47(64)65-28-34(45(62)53-24-16-19-35(53)46(63)52(4)31(3)42(59)48-30(2)44(61)54(36)27-29)50-43(60)33(26-32-17-12-11-13-18-32)49-39(57)20-14-9-7-5-6-8-10-15-21-40(58)51-41-37(55)22-23-38(41)56/h5-15,17-18,20-21,29-31,33-
InChi Key
ODKIYTBYJKALOK-BKZRIAMSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Enopeptin A, originally isolated from a culture broth of Streptomyces sp. RK-1051, is a depsipeptide antibiotic that contains two unusual amino acids (N-methylalanine and 4-methylproline) and features a pentaenone side chain.1,2 It is effective against Gram-positive bacteria, including methicillin-resistant S. aureus (MIC = 25 µg/ml), and Gram-negative bacteria, including mutant forms of E. coli and P. aeruginosa (MICs = 200 µg/ml); however, it is not inhibitory to fungi.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Osada, H., Yano, T., Koshino, H., et al. Enopeptin A, a novel depsipeptide antibiotic with anti-bacteriophage activity. J. Antibiot. (Tokyo) 44(12), 1463-1466 (1991).

    2. Young, J.J., Jung, L.J., Liu, W.T., et al. Solution conformation of enopeptin A, a depsipeptide antibiotic, using 2D NMR and restrained molecular dynamics studies. J. Antibiot. (Tokyo) 47(8), 922-931 (1994).