| Identification | Back Directory | [Name]
PlatensiMycin | [CAS]
835876-32-9 | [Synonyms]
laminomycin
PlatensiMycin
Platensimycin, Streptomyces sp. - CAS 835876-32-9 - Calbiochem
Benzoic acid, 3-[[3-[(1S,3S,4S,5aS,9S,9aR)-1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2-benzoxepin-9-yl]-1-oxopropyl]amino]-2,4-dihydroxy- | [Molecular Formula]
C24H27NO7 | [MDL Number]
MFCD14635440 | [MOL File]
835876-32-9.mol | [Molecular Weight]
441.474 |
| Chemical Properties | Back Directory | [Melting point ]
220-222 °C(Solv: nitromethane (75-52-5)) | [Boiling point ]
683.1±55.0 °C(Predicted) | [density ]
1.47±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble1mg/mL, clear, colorless | [form ]
Tan solid | [pka]
2.14±0.13(Predicted) | [color ]
white to beige | [InChIKey]
CSOMAHTTWTVBFL-OFBLZTNGSA-N |
| Hazard Information | Back Directory | [Uses]
Platensimycin is a broad spectrum gram-positive antibiotic. | [Uses]
Platensimycin is a novel, broad spectrum, Gram-positive antibiotic produced by strains of Streptomyces platensis. Its discovery was heralded by high profile publication and commentary in the scientific and lay press. Platensimycin was discovered by a target-based, whole-cell screening strategy using an antisense differential sensitivity assay, based on the inhibition of fatty acid synthesis. Platensimycin inhibits bacterial growth by selectively inhibiting the elongation enzyme, b-ketoacyl acyl carrier protein synthase (FabF) of the fatty acid synthesis pathway. | [Definition]
ChEBI: A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis a
d exhibits inhibitory activity against fatty acid synthase. | [Enzyme inhibitor]
This thiol-reactive Streptomyces platensis-derived antibiotic (FW = 438.50 g/mol; CAS 835876-32-9), also named 3-[[3-[(1R,3R,4R,5aR,9R,9aS)- 1,4,5,8,9,9a-hexahydro-3,9-dimethyl-8-oxo-3H-1,4:3,5a-dimethano-2- benzoxepin-9-yl]-1-oxopropyl]amino]-2,4-dihydroxybenzoic acid, inhibits Staphylococcus aureus b-ketoacyl-[acyl-carrier-protein] synthase II, or FabF (IC50 = 290 nM). This enzyme, which allows bacteria to produce the fatty acids needed for making cell membranes, is thus a uniquely druggable prokaryotic target. Platensimycin has potent, broad-spectrum Gram-positive activity in vitro and exhibits no cross-resistance to other key antibiotic-resistant bacteria including Methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-intermediate S. aureus, vancomycin-resistant Enterococci, as well as linezolid-resistant and macrolide-resistant pathogens. Platencin is a more potent analogue of Platensimycin. While effective in vivo when continuously administered, its efficacy is reduced when administered by more conventional means. Mechanism of Action: The Cys163 within the FabF active site is activated through the dipole moment of helix N-a-3, lowering its pKa, also increasing its nucleophilicity by the stabilizing effects of FabF’s catalytically required oxyanion hole. Interestingly, the crystal structure complex with platensimycin employed a C163Q mutant which gave a 50-fold increase in apparent binding. |
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