Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E
| Autor: | Justin Cordeil, Jean Legault, Océane Burton, Marie-Christine Groleau, Arianne Provost-Savard, Charles Gauthier, Sabrina Di Cintio, Maude Cloutier, Eric Déziel, Kevin Muru |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Glycan
Glycosylation biology 010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Total synthesis 010402 general chemistry biology.organism_classification 01 natural sciences 0104 chemical sciences Sponge Glycolipid Acetylation Hydrogenolysis Polysaccharides biology.protein Stereoselectivity Glycosides Glycolipids |
| Zdroj: | The Journal of organic chemistry. 86(21) |
| ISSN: | 1520-6904 |
| Popis: | We describe the total synthesis of a chimeric glycolipid bearing both the partially acetylated backbone of sponge-derived agminoside E and the (R)-3-hydroxydecanoic acid chain of bacterial rhamnolipids. The branched pentaglucolipid skeleton was achieved using a [3 + 2] disconnection approach. The β-(1 → 2) and β-(1 → 4)-glycosidic bonds were synthesized through a combination of NIS/Yb(OTf)3- and TMSOTf-mediated stereoselective glycosylations of thiotolyl, N-phenyltrifluoroacetimidate, and trichloroacetimidate donors. Late-stage pentaacetylation, Staudinger reduction of a (2-azidomethyl)benzoyl group, followed by continuous-flow microfluidic hydrogenolysis completed the total synthesis of the structurally simplified glycolipid, whose partial acetylation pattern on the glycan part was identical to agminoside E. Our study lays the foundation for the total synthesis of sponge-derived agminosides and the understanding of their biological functions in sponges. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|