Biomimetic synthesis, antibacterial activity and structure-activity properties of the pyroglutamate core of oxazolomycin

Plamen Angelov, Yui Kwan Sonia Chau, Paul J. Fryer, Mark G. Moloney, Amber L. Thompson, Paul C. Trippier

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Biomimetic intramolecular aldol reactions on oxazolidine templates derived from serine may be used to generate densely functionalised pyroglutamates, which are simpler mimics of the right hand side of oxazolomycin. Some of the compounds from this sequence exhibit in vivo activity against S. aureus and E. coli, suggesting that pyroglutamate scaffolds may be useful templates for the development of novel antibacterials, and cheminformatic analysis has been used to provide some structure-activity data.

Original languageEnglish (US)
Pages (from-to)3472-3485
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number17
DOIs
StatePublished - May 7 2012

Fingerprint

Pyrrolidonecarboxylic Acid
Biomimetics
biomimetics
templates
synthesis
Scaffolds
Serine
Escherichia coli
Hand
diffusomycin
oxazolidine
3-hydroxybutanal

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Biomimetic synthesis, antibacterial activity and structure-activity properties of the pyroglutamate core of oxazolomycin. / Angelov, Plamen; Chau, Yui Kwan Sonia; Fryer, Paul J.; Moloney, Mark G.; Thompson, Amber L.; Trippier, Paul C.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 17, 07.05.2012, p. 3472-3485.

Research output: Contribution to journalArticle

Angelov, Plamen ; Chau, Yui Kwan Sonia ; Fryer, Paul J. ; Moloney, Mark G. ; Thompson, Amber L. ; Trippier, Paul C. / Biomimetic synthesis, antibacterial activity and structure-activity properties of the pyroglutamate core of oxazolomycin. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 17. pp. 3472-3485.
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