Racemic and optically active 2-methoxy-4-oxatetradecanoic acids: Novel synthetic fatty acids with selective antifungal properties

Néstor M. Carballeira, Rosann O'Neill, Keykavous Parang

Research output: Contribution to journalArticlepeer-review

Abstract

The unprecedented (±)-2-methoxy-4-oxatetradecanoic acid and the optically pure (S)-2-methoxy-4-oxatetradecanoic acid were synthesized in six steps and in 11-14% overall yields starting with either 1,2-O-isopropylidene- rac-glycerol or 1,2-O-isopropylidene-(S)-glycerol. The key step in the synthesis was the selective monosilylation of a dibutylstannylene intermediate. The title compounds displayed selective fungitoxicity in the range of 0.08-0.22 mM against Cryptococcus neoformans ATCC 66031 and Aspergillus niger ATCC 16404, but no significant activity against C. albicans ATCC 14053 and ATCC 60193 (>2.6 mM). Albeit being good substrates for N-myristoyltransferases (NMTs), the racemic and the S-enantiomer of the oxygenated 2-methoxylated compounds showed no significant difference in antifungal activity. This finding suggests an alternative mechanism of fungitoxicity other than NMT inhibition.

Original languageEnglish (US)
Pages (from-to)47-54
Number of pages8
JournalChemistry and Physics of Lipids
Volume136
Issue number1
DOIs
StatePublished - Jul 2005
Externally publishedYes

Keywords

  • 2-Methoxy-4-oxatetradecanoic acid
  • Cryptococcus neoformans
  • Fatty acids
  • N-myristoyltransferases

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

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