958
Views
10
CrossRef citations to date
0
Altmetric
Organic Chemistry (Notes)

Total synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C

, , &
Pages 1324-1327 | Received 07 Feb 2014, Accepted 05 Mar 2014, Published online: 17 Jun 2014

References

  • Oettmeier W, Masson K, Soll M, Reil E. Acridones and quinolones as inhibitors of ubiquinone functions in the mitochondrial respiratory chain. Biochem. Soc. Trans. 1994;22:213–216.
  • Friedrich T, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch W, Höfle G, Reichenbach H, Weiss H. Two binding sites for naturally occurring inhibitors in mitochondrial and bacterial NADH: ubiquinone oxidoreductase (Complex I). Biochem. Soc. Trans. 1994;22:226–230.
  • Kunze B, Höfle G, Reichenbach H. The aurachins, new quinoline antibiotics from myxobacteria: production, physico-chemical and biological properties. J. Antibiot. 1987;40:258–265.10.7164/antibiotics.40.258
  • Höfle G, Kunze B. Biosynthesis of aurachins A–L in Stigmatella aurantiaca: a feeding study. J. Nat. Prod. 2008;71:1843–1849.10.1021/np8003084
  • Kitagawa W, Tamura T. A quinoline antibiotic from Rhodococcus erythropolis JCM 6824. J. Antibiot. 2008;61:680–682.10.1038/ja.2008.96
  • Kitagawa W, Ozaki T, Nishioka T, Yasutake Y, Hata M, Nishiyama M, Kuzuyama T, Tamura T. Cloning and heterologous expression of the aurachin RE biosynthesis gene cluster afford a new cytochrome P450 for quinoline N-hydroxylation. ChemBioChem. 2013;14:1085–1093.10.1002/cbic.201300167
  • Yasutake Y, Kitagawa W, Hata M, Nishioka T, Ozaki T, Nishiyama M, Kuzuyama T, Tamura T. Structure of the quinoline N-hydroxylating cytochrome P450 RauA, an essential enzyme that confers antibiotic activity on aurachin alkaloids. FEBS Lett. 2014;588:105–110.10.1016/j.febslet.2013.11.016
  • Lightbown JW, Jackson FL. Inhibition of cytochrome systems of heart muscle and certain bacteria by the antagonists of dihydrostreptomycin: 2-alkyl-4-hydroxyquinoline N-oxides. Biochem. J. 1956;63:130–137.
  • Miyoshi H, Takegami K, Sakamoto K, Mogi T, Iwamura H. Characterization of the ubiquinol oxidation sites in cytochromes bo and bd from Escherichia coli using aurachin C analogues. J. Biochem. 1999;125:138–142.10.1093/oxfordjournals.jbchem.a022250
  • Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 1997;14:605–618.10.1039/np9971400605
  • Li X-W, Herrmann J, Zang Y, Grellier P, Prado S, Müller R, Nay B. Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues. Beilstein J. Org. Chem. 2013;9:1551–1558.10.3762/bjoc.9.176
  • Dejon L, Speicher A. Synthesis of aurachin D and isoprenoid analogues from the myxobacterium Stigmatella aurantiaca. Tetrahedron Lett. 2013;54:6700–6702.10.1016/j.tetlet.2013.09.085
  • Brie M, Silberg LA. Derivatives of pyrazoles. I. Synthesis and IR-Spectra of some new 3-Methyl-5-aryl-pyrazoles. Revue Roumaine de Chimie [Roumanian J. Chem.]. 1989;34:733–737.
  • Kamm O. ß-phenylhydroxylamine. Org. Synth. Colloid. 1941;1:445–447.
  • James AM, Lord MP. Macmillan’s Chemical and Physical Data. London: Macmillan; 1992.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.