Platensimycin
5192329
186947602
2008-01-26T02:26:43Z
Rifleman 82
1255637
promote section
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| IUPACName = 3-<nowiki>[</nowiki>[3-[(1R,3R,4R,5aR,9R,9aS)<br>-1,4,5,8,9,9a-hexahydro-3,9-dimethyl<br>-8-oxo-3H-1,4:3,5a-dimethano<br>-2-benzoxepin-9-yl]-1-oxopropyl]amino]<br>-2,4-dihydroxy-benzoic acid
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| Section2 = {{Chembox Properties
| C=24|H=27|N=1|O=7
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'''Platensimycin''' is a member of a previously unknown class of [[antibiotic]]s, which acts by [[Receptor Antagonist|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 Gram-positive [[bacteria]] need to [[biosynthesis|biosynthesise]] [[cell membrane]]s (β-ketoacyl-(acyl-carrier-protein (ACP)) synthase I/II ([[FabF]]/[[FabB|B]])). 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> Platensimycin is a very effective antibiotic in vivo when continuously administered to cells, however this efficiency is reduced when administered by more conventional means.<ref name=JACS2007>K B. Herath, A B. Attygalle, and S B. Singh (2007) Biosynthetic Studies of Platensimycin. JACS Communications 11/23/2007 PMID 18034483</ref>
The biosynthesis of plantensimycin has been studied using isotope incorporation experiments to show that the benzoic ring is produced from pyruvate and acetate via the [[TCA cycle]], while the C-17 tetracyclic enone acid core is produced from the non-mevalonate terpenoid pathway.<ref name=JACS2007/>
This natural product was first isolated from a strain of ''[[Streptomyces]] platensis'' by the [[Merck & Co.|Merck]] group.<ref name=Wang2006/> 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/>
==References==
<references/>
== External links ==
*[http://news.bbc.co.uk/1/hi/health/4992696.stm BBC News]
*[http://www.smm.org/buzz/buzz_tags/platensimycin Science news stories on Platensimycin]
*[http://www.nature.com/nature/journal/v441/n7091/abs/nature04784.html Abstract in Nature: Platensimycin is a selective FabF inhibitor with potent antibiotic properties]
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