Synthesis of 6-deoxy-d-ido-heptopyranose-containing fragments of the Campylobacter jejuni strain CG8486 capsular polysaccharide

We report here the synthesis of two fragments of the Campylobacter jejuni CG8486 strain CPS that contain a rare 6-deoxy-d-ido-heptopyranose residue and, in one target, two O-methyl phosphoramidate (MeOPN) motifs. The synthetic approach features the stereoselective construction of the β-d-ido-heptopyranoside linkage via glycosylation with a β-d-galacto-heptopyranoside donor followed by a one-pot sequential C-2 and C-3 inversion. During the syntheses, we uncovered a number of interesting conformational effects with regard to the 6-deoxy-ido-heptopyranose ring, the glycosidic linkage connecting the two monosaccharides, and the MeOPN groups.PMID:38354653 | DOI:10.1016/j.carres.2024.109058
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Source Type: research