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P0025

Sigma-Aldrich

Platensimycin

≥90% (HPLC), from Streptomyces platensis

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About This Item

Empirical Formula (Hill Notation):
C24H27NO7
CAS Number:
835876-32-9
Molecular Weight:
441.47
UNSPSC Code:
12161606
PubChem Substance ID:
329819980

biological source

Streptomyces platensis

Assay

≥90% (HPLC)

form

solid

color

white to beige

solubility

DMSO: 1 mg/mL, clear, colorless

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

O=C1C=C[C@]2(C[H])[C@H]3CC[C@@](O3)([H])C2C1CCC(CNC4=C(O)C=CC(C(O)=O)=C4O)=O

InChI

1S/C22H25NO7/c1-22-9-8-14(25)12(18(22)16-6-7-17(22)30-16)3-2-11(24)10-23-19-15(26)5-4-13(20(19)27)21(28)29/h4-5,8-9,12,16-18,23,26-27H,2-3,6-7,10H2,1H3,(H,28,29)/t12?,16-,17+,18?,22+/m0/s1

InChI key

IGBNLKVUOHQLTO-MBQNLBDGSA-N

Application

Platensimycin (PTM) is a broad-spectrum antibiotic produced by LStreptomyces platensis. Platensimycin is used to inhibit lipid biosynthesis. It is used in diabetes research and to study the potential treatment of metabolic disorders[1].

Biochem/physiol Actions

Demonstrates no cross-resistance to other antibiotic-resistant bacteria, including MRSA (methicillin-resistant Staphylococcus aureus).
Mode of action: Selectively inhibits lipid biosynthesis by targeting FabF/B within the fatty acid synthesis pathway.
Antimicrobial spectrum: Gram-positive bacteria.
Platensimycin selectively inhibits the elongation-condensing enzymes FabF/B of the fatty acid biosynthesis pathway in bacteria. PTM is a potent and highly selective inhibitor of mammalian fatty acid synthase. Platensimycin specifically inhibits fatty acid synthesis but not sterol synthesis in rat primary hepatocytes[1]. It is thought that the thiol group of FabF Cys163 may be activated through the dipole moment of helix N-α-3 which lowers the pKa[2]. It does not demonstrate cross-resistance to other antibiotic-resistant bacteria, including MRSA (methicillin-resistant Staphylococcus aureus). It is active against Gram-positive bacteria.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
080M1277

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