Beilstein J. Org. Chem.2019,15, 685–694, doi:10.3762/bjoc.15.63
: O4–C1–O1–CH2 torsion was set to +60° or −60° depending on α- or β-configuration of the sugar in accordance with the exo-anomericeffect. Other starting torsions in the propyl group had trans-orientation. Geometry optimizations of all the thus obtained structures were carried out at ab initio HF/6-311
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Scheme 1:
Studied monosaccharides 1–3 and 1s–3s and their preparation.
Beilstein J. Org. Chem.2014,10, 2215–2221, doi:10.3762/bjoc.10.229
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-anomericeffect) 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-anomericeffect; macrolide
and foremost, the axial (5) versus equatorial (6) positioning of the anomeric oxygen, and subsequently the aglycone, dictates the orientation of the D-glucose- and macrocyclic planes. Relatedly the exo-anomericeffect [28][29] plays a role in determining the orientation of the backbone of the
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Graphical Abstract
Figure 1:
Erythromycin (1), the archetypal macrolide; sophorlipid lactone 2, a glycolipid macrolactone; β-D-g...