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Total synthesis of the proposed structures of gladiosides I and II.

Authors :
Hussain N
Delar E
Piochon M
Groleau MC
Tebbji F
Sellam A
Déziel E
Gauthier C
Source :
Carbohydrate research [Carbohydr Res] 2021 Sep; Vol. 507, pp. 108373. Date of Electronic Publication: 2021 Jun 11.
Publication Year :
2021

Abstract

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.<br /> (Copyright © 2021 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1873-426X
Volume :
507
Database :
MEDLINE
Journal :
Carbohydrate research
Publication Type :
Academic Journal
Accession number :
34157641
Full Text :
https://doi.org/10.1016/j.carres.2021.108373