Dépôt numérique

Total synthesis of the proposed structures of gladiosides I and II

Hussain, Nazar, Delar, Emmanilo, Piochon, Marianne, Groleau, Marie-Christine, Tebbji, Faiza, Sellam, Adnane, Déziel, Éric ORCID: https://orcid.org/0000-0002-4609-0115 et Gauthier, Charles ORCID: https://orcid.org/0000-0002-2475-2050 (2021). Total synthesis of the proposed structures of gladiosides I and II Carbohydrate Research , vol. 507 , nº 108373. p. 1-12. DOI: 10.1016/j.carres.2021.108373.

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Burkholderia gladioli is a Gram-negative bacterium that biosynthesizes a cocktail of potent antimicrobial compounds, including the antifungal phenolic glycoside sinapigladioside. Herein, we report the total synthesis of the proposed structures of gladiosides I and II, two structurally related phenolic glycosides previously isolated from B. gladioli OR1 cultures. Importantly, the physical and analytical data of the synthetic compounds were in significant discrepancies with the natural products suggesting a misassignment of the originally proposed structures. Furthermore, we have uncovered an acid-catalyzed fragmentation mechanism converting the α,β-unsaturated methyl carbamate-containing gladioside II into the aldehyde-containing gladioside I. Our results lay the foundation for the expeditious synthesis of derivatives of these Burkholderia-derived phenolic glycosides, which would enable to decipher their biological roles and potential pharmacological properties.

Type de document: Article
Mots-clés libres: Burkholderia Gladioli; Gladioside; Phenolic Glycoside; Structural Misassignment; Total Synthesis
Centre: Centre INRS-Institut Armand Frappier
Date de dépôt: 23 juin 2022 02:28
Dernière modification: 23 juin 2022 02:28
URI: https://espace.inrs.ca/id/eprint/12352

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