835876-32-9

Basic information

• Product Name: PlatensiMycin
• Synonyms: PlatensiMycin
• CAS NO: 835876-32-9
• Molecular Formula: C₂₄H₂₇NO₇
• Molecular Weight: 441.47368
• Mol File: 835876-32-9.mol

Chemical Properties

• Appearance: white to beige/
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble1mg/mL, clear, colorless
• CAS DataBase Reference: PlatensiMycin(CAS DataBase Reference)
• NIST Chemistry Reference: PlatensiMycin(835876-32-9)
• EPA Substance Registry System: PlatensiMycin(835876-32-9)

Safety Data

• Hazardous Substances Data: 835876-32-9(Hazardous Substances Data)

Usage

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.

Upstream product

• 1109175-39-4 C₂₉H₃₉NO₇Si 
• 1041186-50-8 C₁₃H₁₅NO₂ 
• 1041186-27-9 C₁₀H₁₁NO₂ 
• 1041186-43-9 C₁₀H₁₀INO₂ 
• 1041186-47-3 C₉H₁₀INO₂ 
• 1023284-62-9 platensic acid 
• 1197042-84-4 C₁₄H₁₈O₂ 
• 1041186-51-9 C₁₃H₁₈O₃ 
• 1041186-34-8 C₁₀H₁₀IN₃O₂ 
• 1041186-48-4 C₁₃H₁₈INO₂S 
• 948914-61-2 platensimycin methyl ester 

Related news

In vivo instability of PlatensiMycin (cas 835876-32-9) and platencin: Synthesis and biological evaluation of urea- and carbamate-PlatensiMycin (cas 835876-32-9)07/16/2019

Platensimycin (PTM) and platencin (PTN), two natural products and promising drug leads that target bacterial and mammalian fatty acid synthases, are known to have unfavorable pharmacokinetic properties. It is not clear, however, what the metabolic fates of PTM and PTN are and no efforts have bee...detailed

Antibacterial sulfur-containing PlatensiMycin (cas 835876-32-9) and platencin congeners from Streptomyces platensis SB1202907/15/2019

The platensimycin (PTM) and platencin (PTN) class of natural products are promising drug leads that target bacterial and mammalian fatty acid synthases. Natural congeners and synthetic analogues of PTM and PTN have been instrumental in determining their structure–activity relationships, with on...detailed

Relevant articles and documents

Novel Platensimycin Derivatives, Their Intermediates, and Process for Preparing the Same, and New Process for Preparing Platensimycin

The present invention relates to novel platensimycin derivatives, their intermediates and preparing methods of the same. Platensimycin is known as an effective antibiotic material having a broad antimicrobial spectrum and its derivatives are also expected to be effective antibiotic candidates. The present invention also relates to a novel preparing method of platensimycin. The intermediates used for the production of platensimycin and its derivatives of the present invention are tricyclo ketone derivatives and tetracyclo derivatives. Tetracyclo derivatives are prepared from tricyclo ketone derivatives prepared by carbonyl ylide [3+2] cycloaddition of dia-zoketone derivative.

NOVEL PLATENSIMYCIN DERIVATIVES, THEIR INTERMEDIATES, AND PROCESS FOR PREPARARING THE SAME, AND NEW PROCESS FOR PREPARING PLATENSIMYCIN

The present invention relates to novel platensimycin derivatives, their intermediates and preparing methods of the same. Platensimycin is known as an effective antibiotic material having a broad antimicrobial spectrum and its derivatives are also expected to be effective antibiotic candidates. The present invention also relates to a novel preparing method of platensimycin. The intermediates used for the production of platensimycin and its derivatives of the present invention are tricyclo ketone derivatives and tetracyclo derivatives. Tetracyclo derivatives are prepared from tricyclo ketone derivatives prepared by carbonyl ylide [3+2] cycloaddition of dia- zoketone derivative

Total synthesis of (-)-platensimycin, a novel antibacterial agent

An enantioselective synthesis of platensimycin, a novel antibiotic natural product that inhibits bacterial β-ketoacyl-(acyl-carrier-protein) synthase (FabF), is described. Our synthetic strategy for the construction of the oxatetracyclic core involved an