10203. Platensimycin
Nomenclature
CAS number: 835876-32-9
3-[[3-[(1S,3S,4S,5aS,9S,9aR)-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. C24H27NO7; mol wt 441.47.
C 65.29%, H 6.16%, N 3.17%, O 25.37%.
Description and references
Broad spectrum antibiotic produced by Streptomyces platensis. Inhibits gram-positive bacterial growth by selective inhibition of the condensing enzyme, FabF in type II bacterial fatty acid biosynthesis. Discovery and characterization: J. Wang et al., Nature 441, 358 (2006) DOI PubMed. Isoln, structure determn and stereochemistry: S. B. Singh et al., J. Am. Chem. Soc. 128, 11916 (2006) DOI PubMed. Total synthesis of racemic form: K. C. Nicolaou et al., Angew. Chem. Int. Ed. 45, 7086 (2006) DOI PubMed. Review of mechanism of action: D. Hbich, F. von Nussbaum, ChemMedChem 1, 951-954 (2006) DOI PubMed.
