De novo macrolide-glycolipid macrolactone hybrids: Synthesis, structure and antibiotic activity of carbohydrate-fused macrocycles

Richard T. Desmond, Anniefer N. Magpusao, Chris Lorenc, Jeremy B. Alverson, Nigel Priestley, Mark W. Peczuh

Research output: Contribution to journalArticlepeer-review

Abstract

Natural product-like macrocycles were designed as potential antibacterial compounds. The macrocycles featured a D-glucose unit fused into a 12- or 13-member macrolactone. The rings are connected via the C6' and anomeric (C1') positions of the monosaccharide. The new macrocycles/macrolides were characterized by X-ray crystallography. Their structures showed that, in addition to the ester and alkene units, the dihedral angle about the glycosidic linkage (exo-anomeric effect) influenced the overall shape of the molecules. Glycosylation of an available hydroxy group on the macrocycle gave a hybrid macrolide with features common to erythromycin and sophorlipid macrolactone. Weak antibiotic activity (MICs <100 μg/mL) was observed for several of the compounds.

Original languageEnglish
Pages (from-to)2215-2221
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
StatePublished - Sep 17 2014

Keywords

  • Antibiotic
  • Carbohydrate
  • Exo-anomeric effect
  • Macrolide
  • Structure
  • Synthesis

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