869898-86-2

Usage

Uses

Used in Pharmaceutical Industry:
Platencin is used as a potent antibiotic for targeting FabF and FabH proteins, which are essential in bacterial fatty acid synthesis. Its ability to inhibit both FabF and FabH makes it more effective than its analogue, platensimycin, which only targets FabF. This dual targeting mechanism contributes to platencin's potential in combating antibiotic-resistant bacteria, including methicillin-resistant S. aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococci.
Used in Antibiotic Resistance Management:
Platencin is used as a novel antibiotic to address the growing issue of antibiotic resistance. Its unique mechanism of action, targeting both FabF and FabH, helps in overcoming the limitations of existing antibiotics and provides an alternative for treating infections caused by resistant bacterial strains. This makes platencin a valuable asset in the development of new antibiotics to manage and control antibiotic resistance.

Enzyme inhibitor

This antibiotic (FW = 425.2 g/mol; CAS 869898-86-2; Soluble in ethanol, methanol, DMF or DMSO) inhibits both Staphylococcus aureus b-ketoacyl- [acyl-carrier-protein] synthases II and III, with IC50 values of 1.95 and 3.91 μg/mL, respectively. Platencin exhibits strong, broad-spectrum, Grampositive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium, without evidence of toxicity in humans.

Upstream product

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• 1020070-68-1 (1S,5S,6S,8S)-5-methyl-9-methylenetricyclo[6.2.2.0(1,6)]dodec-2-en-4-one 
• 1020070-43-2 (1R,6S,8S)-9-methylidenetricyclo[6.2.2.0(1,6)]dodec-2-en-4-one 
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Relevant academic research and scientific papers

A nine-step total synthesis of (-)-platencin

Within 1 year, platencin, a recently discovered antibiotic, has become a highly competitive synthetic target, due to its promising bioactivity and its unusual complex molecular architecture. Herein, a particularly concise total synthesis of platencin star

A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin

The natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant analogues. The key step involves a thermally promoted and facially selective intramolecular Diels-Alder (IMDA) cycloaddition reaction to give an adduct that embodies the tricarbocyclic core of (-)-platencin. This adduct was elaborated over thirteen steps to the natural product. The substrate for the IMDA reaction was prepared by Stille cross-coupling of a Z-configured alkenylstannane with an iodinated diene obtained in an enantiomerically pure form through the whole-cell biotransformation of iodobenzene.

Total synthesis and biological evaluation of the fab-inhibitory antibiotic platencin and analogues thereof

In this article, application of the masked o-benzoquinone intramolecular Diels-Alder reaction in the total synthesis of platencin (2), a recently reported Fab inhibitory antibiotic, is described. Through intelligence gathering, the evolving strategies ult

Total synthesis of (±)-platencin

A novel route to (±)-platencin is reported, in which the highly stereoselective alkylative quaternization of a cyclohexenone scaffold via 1,4-diastereoinduction and two radical carbon-carbon bond-forming reactions that involve titanium(III)-mediated cycli

Total syntheses of (±)-platencin and (-)-platencin

The secondary metabolites platensimycin and platencin, isolated from the bacterial strain Streptomyces platensis, represent a novel class of natural products exhibiting unique and potent antibacterial activity. Platencin, though structurally similar to platensimycin, has been found to operate through a slightly different mechanism of action involving the dual inhibition of lipid elongation enzymes FabF and FabH. Both natural products exhibit strong, broad-spectrum, Gram-positive antibacterial activity to key antibiotic resistant strains, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate S. aureus, and vancomycin-resistant Enterococcus faecium. Described herein are our synthetic efforts toward platencin, culminating in both racemic and asymmetric preparation of the natural product. The syntheses demonstrate the power of the cobalt-catalyzed asymmetric Diels-Alder reaction and the one-pot reductive rearrangement of [3.2.1] bicyclic ketones to [2.2.2] bicyclic olefins.

Total synthesis of platencin

(Chemical Equation Presented) The asymmetric total synthesis of the newly discovered and potent antibiotic platencin has been achieved. The approach makes use of an asymmetric Diels-Alder reaction, a gold(I)-catalyzed cyclization, and a homoallyl radical rearrangement to forge the polycyclic architecture of this intriguing target (see scheme, SEM=2-(trimethylsilyl)ethoxymethyl).

Total synthesis of (±)-platencin

(Chemical Equation Presented) Resistant bacteria - beware! Platencin, a structurally novel broad-spectrum antibacterial agent, was the target of a total synthesis from o-anisic acid (see scheme). A Diels-Alder reaction with an a-substituted cyclohexenone as well as a [Ni-(cod)2]-promoted 1,4-addition enables the concise and stereocontrolled formation of the core. A protecting group free coupling with an aniline unit completed the synthesis. cod = 1,5-cyclooctadiene.