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Platensimycin (Molecule of the Month for October 2006)


Platensimycin is an antibiotic, it is the first of a new class of antibiotics in over 40 years. It was discovered by Merck scientist Jun Wang and over 35 of his Merck colleagues, after they systematically screened 250,000 compounds extracted from microorganisms for antibiotic properties, Platensimycin, isolated from a strain of bacterium Streptomyces platensis found in a soil sample from South Africa.

Platensimycin works by inhibiting a bacterium ability to synthesize fatty acids--the essential components of cell membranes. The anti-bacterial effect is through the selective targeting of FabF/ B condensing enzymes in the synthetic pathway of fatty acids. Direct binding assays show that platensimycin interacts specifically with the acylenzyme intermediate of the target protein.

Platensimycin demonstrates strong, broad-spectrum Gram-positive antibacterial activity by selectively inhibiting cellular lipid biosynthesis. Treatment with platensimycin eradicates Staphylococcus aureus infection in mice. Because of its unique mode of action, platensimycin shows no cross-resistance to other key antibiotic-resistant strains tested, including methicillin-resistant S. aureus, vancomycin-intermediate S. aureus and vancomycin-resistant enterococci. Platensimycin is the most potent inhibitor reported for the FabF/ B condensing enzymes, and is the only inhibitor of these targets that shows broad-spectrum activity, in vivo efficacy and no observed toxicity.

Formal Chemical Name (IUPAC)
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-dihydroxy-benzoic acid




Picture of Platensimycin

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Platensimycin structure
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Picture of Platensimycin

C24 H27 N O7

Update by Karl Harrison
(Molecule of the Month for October 2006 )