Platensimycin: Difference between revisions
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'''Platensimycin''' is a member of a previously unknown class of [[antibiotic]]s, which acts by | '''Platensimycin''' is a member of a previously unknown class of [[antibiotic]]s, which acts by blocking [[enzyme]]s involved in the of the condensation steps in [[fatty acid]] biosynthesis,<ref>Dieter Häbich, Franz von Nussbaum, ''ChemMedChem'' '''2006''', ''1'', 951–954. Platensimycin, a new antibiotic and "superbug challenger" from nature. PMID 16952137</ref> which [[bacteria]] need to [[biosynthesis|biosynthesise]] [[cell membrane]]s (β-ketoacyl-(acyl-carrier-protein (ACP)) synthase I/II (FabF/FabB). Other enzymes in this pathway have similarly been proven antibiotic targets for example FabI, the enoyl-ACP (acyl carrier protein) reductase, that is inhibited by [[isoniazid]] and related compounds and the antiseptic agent [[triclosan]].<ref>H T. Wright, and K.A Reynolds (2007) Antibacterial targets in fatty acid biosynthesis. Current Opinion in Microbiology doi:10.1016/j.mib.2007.07.001</ref> It is an experimental new drug in [[Pre-clinical development|preclinical trials]] in an effort to combat [[MRSA]] in a mouse [[Animal model|model]].<ref name=Wang2006>Jun Wang ''et al'', ''Platensimycin is a selective FabF inhibitor with potent antibiotic properties'', Nature 441, 358-361 (18 May 2006) PMID 16710421</ref> The newly discovered natural product inhibitor was first isolated from a strain of ''[[Streptomyces]] platensis'' by the [[Merck & Co.|Merck]] group.<ref name=Wang2006/> | ||
Recently, a first total synthesis of racemic platensimycin has been published.<ref name=Nicolaou2006>K. C. Nicolaou, A. Li, D. J. Edmonds, ''Angew. Chem.'' '''2006''', ''118'', 7244 – 7248; ''Angew. Chem. Int. Ed.'' '''2006''', ''45'', 7086 – 7090. PMID 17013803</ref> Its structure consists of a 3-amino-2,4-dihydroxybenzoic acid polar part linked through an amine bond to a lipophilic pentacyclicketolide.<ref name=Nicolaou2006/> | Recently, a first total synthesis of racemic platensimycin has been published.<ref name=Nicolaou2006>K. C. Nicolaou, A. Li, D. J. Edmonds, ''Angew. Chem.'' '''2006''', ''118'', 7244 – 7248; ''Angew. Chem. Int. Ed.'' '''2006''', ''45'', 7086 – 7090. PMID 17013803</ref> Its structure consists of a 3-amino-2,4-dihydroxybenzoic acid polar part linked through an amine bond to a lipophilic pentacyclicketolide.<ref name=Nicolaou2006/> | ||
Revision as of 14:01, 14 May 2009
| Template:Chembox header| Platensimycin | |
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| Chemical name | 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 |
| Molecular formula | C24H27NO7 |
| Molar mass | 441.18 g/mol |
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Platensimycin is a member of a previously unknown class of antibiotics, which acts by blocking enzymes involved in the of the condensation steps in fatty acid biosynthesis,[1] which bacteria need to biosynthesise cell membranes (β-ketoacyl-(acyl-carrier-protein (ACP)) synthase I/II (FabF/FabB). Other enzymes in this pathway have similarly been proven antibiotic targets for example FabI, the enoyl-ACP (acyl carrier protein) reductase, that is inhibited by isoniazid and related compounds and the antiseptic agent triclosan.[2] It is an experimental new drug in preclinical trials in an effort to combat MRSA in a mouse model.[3] The newly discovered natural product inhibitor was first isolated from a strain of Streptomyces platensis by the Merck group.[3]
Recently, a first total synthesis of racemic platensimycin has been published.[4] Its structure consists of a 3-amino-2,4-dihydroxybenzoic acid polar part linked through an amine bond to a lipophilic pentacyclicketolide.[4]
References
- ↑ Dieter Häbich, Franz von Nussbaum, ChemMedChem 2006, 1, 951–954. Platensimycin, a new antibiotic and "superbug challenger" from nature. PMID 16952137
- ↑ H T. Wright, and K.A Reynolds (2007) Antibacterial targets in fatty acid biosynthesis. Current Opinion in Microbiology doi:10.1016/j.mib.2007.07.001
- ↑ 3.0 3.1 Jun Wang et al, Platensimycin is a selective FabF inhibitor with potent antibiotic properties, Nature 441, 358-361 (18 May 2006) PMID 16710421
- ↑ 4.0 4.1 K. C. Nicolaou, A. Li, D. J. Edmonds, Angew. Chem. 2006, 118, 7244 – 7248; Angew. Chem. Int. Ed. 2006, 45, 7086 – 7090. PMID 17013803
External links
- BBC News
- Science news stories on Platensimycin
- Abstract in Nature: Platensimycin is a selective FabF inhibitor with potent antibiotic properties