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P0025

Sigma-Aldrich

Platensimycin

≥90% (HPLC), from Streptomyces platensis

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About This Item

Formule empirique (notation de Hill) :
C24H27NO7
Numéro CAS:
835876-32-9
Poids moléculaire :
441.47
Code UNSPSC :
12161606
ID de substance PubChem :
329819980
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Source biologique

Streptomyces platensis

Essai

≥90% (HPLC)

Forme

solid

Couleur

white to beige

Solubilité

DMSO: 1 mg/mL, clear, colorless

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria

Mode d’action

enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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].

Actions biochimiques/physiologiques

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.
Selectively inhibits lipid biosynthesis by targeting FabF/B within the fatty acid synthesis pathway.

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
080M1277

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Makoto Hibi et al.
Communications biology, 4(1), 16-16 (2021-01-06)
The high-valent iron-oxo species formed in the non-heme diiron enzymes have high oxidative reactivity and catalyze difficult chemical reactions. Although the hydroxylation of inert methyl groups is an industrially promising reaction, utilizing non-heme diiron enzymes as such a biocatalyst has
Yuta Tsunematsu et al.
Journal of the American Chemical Society, 143(1), 206-213 (2020-12-23)
Epidithiodiketopiperazines (ETPs) are a class of ecologically and medicinally important cyclodipeptides bearing a reactive transannular disulfide bridge. Aspirochlorine, an antifungal and toxic ETP isolated from Aspergillus oryzae used in sake brewing, deviates from the common ETP scaffold owing to its
Kenzie A Clark et al.
Journal of the American Chemical Society, 141(27), 10610-10615 (2019-06-28)
The biosynthetic pathways of microbial natural products provide a rich source of novel enzyme-catalyzed transformations. Using a new bioinformatic search strategy, we recently identified an abundance of gene clusters for ribosomally synthesized and post-translationally modified peptides (RiPPs) that contain at
Szu-Yi Hsu et al.
ACS synthetic biology, 8(10), 2397-2403 (2019-09-06)
Serofendic acid is a natural neuroprotective molecule found in fetal calf serum. It is able to protect neurons against mechanisms of cell death associated with neurodegenerative disease. Because only trace quantities are present in fetal calf serum and complete chemical
Allen C Price et al.
Journal of bacteriology, 185(14), 4136-4143 (2003-07-03)
The beta-ketoacyl-acyl carrier protein synthases are members of the thiolase superfamily and are key regulators of bacterial fatty acid synthesis. As essential components of the bacterial lipid metabolic pathway, they are an attractive target for antibacterial drug discovery. We have
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