Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti

Research output: Contribution to journalArticleResearchpeer review

Authors

  • Rolf Jansen
  • Klaus Gerth
  • Heinrich Steinmetz
  • Silke Reinecke
  • Wolfgang Kessler
  • Andreas Kirschning
  • Rolf Müller

External Research Organisations

  • Helmholtz Centre for Infection Research (HZI)
  • Saarland University
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Details

Original languageEnglish
Pages (from-to)7739-7744
Number of pages6
JournalChemistry - A European Journal
Volume17
Issue number28
Publication statusPublished - 30 May 2011

Abstract

Hen or egg? The polyketide-based p-quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1-A3 was observed. Under mild acidic conditions a Grob-type fragmentation of elansolid A3 led to the p-hydroxy styryl isomer elansolid D.

Keywords

    antibiotics, Chitinophaga sancti, Grob fragmentation, molecular modeling, quinone methide

ASJC Scopus subject areas

Cite this

Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti. / Jansen, Rolf; Gerth, Klaus; Steinmetz, Heinrich et al.
In: Chemistry - A European Journal, Vol. 17, No. 28, 30.05.2011, p. 7739-7744.

Research output: Contribution to journalArticleResearchpeer review

Jansen, R, Gerth, K, Steinmetz, H, Reinecke, S, Kessler, W, Kirschning, A & Müller, R 2011, 'Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti', Chemistry - A European Journal, vol. 17, no. 28, pp. 7739-7744. https://doi.org/10.1002/chem.201100457
Jansen, R., Gerth, K., Steinmetz, H., Reinecke, S., Kessler, W., Kirschning, A., & Müller, R. (2011). Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti. Chemistry - A European Journal, 17(28), 7739-7744. https://doi.org/10.1002/chem.201100457
Jansen R, Gerth K, Steinmetz H, Reinecke S, Kessler W, Kirschning A et al. Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti. Chemistry - A European Journal. 2011 May 30;17(28):7739-7744. doi: 10.1002/chem.201100457
Jansen, Rolf ; Gerth, Klaus ; Steinmetz, Heinrich et al. / Elansolid A3, a unique p-quinone methide antibiotic from Chitinophaga sancti. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 28. pp. 7739-7744.
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