'Click' synthesis of triazole-based spirostan saponin analogs
Novel analogs of spirostan saponins in which the glycosidic bond has been replaced by a triazole linkage are described. For this, a direct oligosaccharide-steroid conjugation approach based on the CuI- catalyzed azide-alkyne 1,3-dipolar cycloaddition was implemented, leading to diverse combinations of saponin analogs with variations in the trisaccharide moiety, the artificial linkage, and the steroid-skeleton functionalization. This 'click' process proved great efficiency for the ligation of two bulky building blocks (e.g., chacotriose derivatives and spirostanes bearing axial azides), which enabled the rapid creation of a small library of triazole-based analogs for cytotoxicity evaluation. A molecular modeling study was performed to understand the conformational and electronic differences between a natural saponin and its triazole-based analogs.
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | artículo biblioteca |
| Published: |
Elsevier
2011-10-07
|
| Subjects: | Steroids, Carbohydrates, Saponins, Click chemistry, Cycloaddition reactions, |
| Online Access: | http://hdl.handle.net/10261/199643 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003767 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|