A cyclic thiopeptide antibiotic
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Berninamycin A

Item No. 18769

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-threonyl-2-[(1Z)-1-amino-1-propen-1-yl]- 5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-3-methyl-L-threonyl-2-(1-aminoethenyl)- 5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-6-[2-(1-aminoethenyl)- 4-oxazolyl]-5-(4-carboxy-2-thiazolyl)-2-pyridinecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide (7→1)-lactam
CAS Number
58798-97-3
Molecular Formula
C51H51N15O15S
Formula Weight
1146.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: moderately soluble
SMILES
O=C(NC(C(NC(C(N)=O)=C)=O)=C)C1=CC=C(C2=NC(C(N[C@]([C@@H](C)O)([H])C(N/C(C3=NC4=C(C)O3)=C\C)=O)=O)=CS2)C(C5=COC(C(NC(C(NC(C6=C(C)OC(C(NC([C@@H](NC(C(NC4=O)=C)=O)C(C)(O)C)=O)=C)=N6)=O)=C)=O)=C)=N5)=N1
InChi Code
InChI=1S/C51H51N15O15S/c1-13-28-49-65-34(26(10)81-49)45(76)56-21(5)40(71)66-36(51(11,12)78)46(77)58-23(7)48-64-33(25(9)80-48)44(75)55-20(4)39(70)57-22(6)47-61-30(16-79-47)35-27(50-62-31(17-82-50)42(73)63-32(24(8)67)43(74)60-28)14-15-29(59-35)41(72)54
InChi Key
CAFFHXXVDGAVPH-DKFXDEMXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $316

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    $1,333

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    Product Description

    Berninamycin A is a cyclic thiopeptide antibiotic first isolated from S. bernensis.1 It inhibits protein biosynthesis in Gram positive bacteria through binding with ribosomal subunits.1,2 Cyclic thiopeptide antibiotics, including berninamycin A, induce the transcriptional activator TipA in Streptomyces.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lau, R.C.M., and Rinehart, K.L. Berninamycins B, C, and D, minor metabolites from Streptomyces bernensis. J. Antibiot. (Tokyo) 47(12), 1466-1472 (1994).

    2. Thompson, J., Cundliffe, E., and Stark, M.J.R. The mode of action of berninamycin and mechanism of resistance in the producing organism, Streptomyces bernensis. J. Gen. Microbiol. 128(4), 875-884 (1982).

    3. Chiu, M.L., Folcher, M., Katoh, T., et al. Broad spectrum thiopeptide recognition specificity of the Streptomyces lividans TipAL protein and its role in regulating gene expression. The Journal of Biological Chemisty 274(29), 20578-20586 (1999).