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 language | English |
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Pages (from-to) | 2215-2221 |
Number of pages | 7 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 10 |
DOIs | |
State | Published - Sep 17 2014 |
Keywords
- Antibiotic
- Carbohydrate
- Exo-anomeric effect
- Macrolide
- Structure
- Synthesis