Intra- and Intermolecular Glycosylation of d-Idopyranosyl and 6-Deoxy-d-ido-heptopyranosyl Donors: Toward the Repeating Unit of Campylobacter jejuni HS:4c Capsular Polysaccharide

Cloutier, Maude; Verma, Nitish; Douchez, Ilona et Gauthier, Charles ORCID: https://orcid.org/0000-0002-2475-2050 (2025). Intra- and Intermolecular Glycosylation of d-Idopyranosyl and 6-Deoxy-d-ido-heptopyranosyl Donors: Toward the Repeating Unit of Campylobacter jejuni HS:4c Capsular Polysaccharide European Journal of Organic Chemistry , vol. 29 , nº 4. pp. 1-13. DOI: 10.1002/ejoc.202500894.

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Résumé

The synthesis of disaccharide mimics of Campylobacter jejuni HS:4c capsular polysaccharide, a major pathogen associated with campylobacteriosis, is challenged by the presence of a 1,2-cis-β-linked 6-deoxy-d-ido-heptopyranoside. Herein, the development of a synthetic route to orthogonally protected d-ido-hexo- and 6-deoxy-d-ido-heptopyranosyl donors is reported bearing diverse anomeric leaving groups, which represents, to the best of knowledge, the second direct access to 6-deoxy-d-ido-heptopyranosides from ido-configured precursors. These donors were evaluated in intramolecular aglycon delivery (IAD) and intermolecular glycosylation protocols. While IAD enabled complete β-stereoselectivity with hexosyl donors, it failed with the heptosyl analog. Intermolecular glycosylation provided mixtures of anomers, but the use of a 7-O-acetyl-protected heptosyl donor allowed access to the disaccharide in good yield, with chromatographic separation of the α- and β-anomers. Structural analysis revealed unexpected conformational behavior, with the α-disaccharide adopting the 1C4 chair conformation. This work establishes a foundation for the synthesis of C. jejuni HS:4c disaccharides and represents a step toward well-defined sugar-based vaccines candidates against campylobacteriosis. © 2025 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbH.

Type de document:	Article
Informations complémentaires:	Document e202500894. This work was supported by the Natural Sciences and Engineering Research Council of Canada (RGPIN-2022−04515, to C.G), Programmes Transversaux de Recherche (PTR 380−20, to C.G).
Mots-clés libres:	6-deoxy-ido-heptose; Campylobacter jejuni; capsular polysaccharides; disaccharide; intramolecular glycosylation
Centre:	Centre INRS-Institut Armand Frappier
Date de dépôt:	16 juin 2026 14:58
Dernière modification:	16 juin 2026 14:58
URI:	https://espace.inrs.ca/id/eprint/16789

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