@article{0e7a153b0c624b829dca5facd23f6320,
title = "De novo macrolide-glycolipid macrolactone hybrids: Synthesis, structure and antibiotic activity of carbohydrate-fused macrocycles",
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.",
keywords = "Antibiotic, Carbohydrate, Exo-anomeric effect, Macrolide, Structure, Synthesis",
author = "Desmond, \{Richard T.\} and Magpusao, \{Anniefer N.\} and Chris Lorenc and Alverson, \{Jeremy B.\} and Nigel Priestley and Peczuh, \{Mark W.\}",
note = "Publisher Copyright: {\textcopyright} 2014 Desmond et al; licensee Beilstein-Institut.",
year = "2014",
month = sep,
day = "17",
doi = "10.3762/bjoc.10.229",
language = "English",
volume = "10",
pages = "2215--2221",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",
}