Synthesis of Heparan Sulfate- and Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l -Iduronic Lactone Thioglycosides
| Autor: | John M. Gardiner, Charlotte E. Dalton, Robin A. Jeanneret |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Glycosylation
Anomer Iduronic Acid Stereochemistry Dermatan Sulfate Oligosaccharides 010402 general chemistry 01 natural sciences Chemical synthesis Dermatan sulfate Glycosaminoglycan Lactones chemistry.chemical_compound Carbohydrate Conformation chemistry.chemical_classification Sulfates 010405 organic chemistry Organic Chemistry Heparan sulfate 0104 chemical sciences carbohydrates (lipids) chemistry Thioglycosides Carbohydrate conformation Lactone |
| Zdroj: | The Journal of Organic Chemistry. 84:15063-15078 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Heparan sulfate (HS) and dermatan sulfate (DS) are l-iduronic acid containing glycosaminoglycans (GAGs) which are implicated in a number of biological processes and conditions including cancer and viral infection. Chemical synthesis of HS and DS is required to generate structurally defined oligosaccharides for a biological study. Herein, we present a new synthetic approach to HS and DS oligosaccharides using chemoselective glycosylation which relies on a disarmed [2.2.2] l-ido lactone motif. The strategy provides a general approach for iterative-reducing end chain extension, using only shelf-stable thioglycoside building blocks, exploiting a conformational switch to control reactivity, and thus requires no anomeric manipulation steps between glycosylations. |
| Databáze: | OpenAIRE |
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