'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Novel analogs of spirostan saponins in which the glycosidic bond has been replaced by a triazole linkage are described.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: | Pérez-Labrada, Karell, Brouard, Ignacio, Morera, Cercis, Estévez, Francisco, Bermejo, Jaime, Rivera, Daniel G. |
---|---|
Other Authors: | Consejo Superior de Investigaciones Científicas (España) |
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!
|
Similar Items
-
Synthesis and conformational study of triazole-linked bis-spirostanic conjugates
by: Pérez-Labrada, Karell, et al.
Published: (2013-03-20) -
Combined Ugi-4CR/CuAAC approach to triazole-based neoglycolipids
by: Pérez-Labrada, Karell, et al.
Published: (2014-06) -
Geranyl functionalized materials for site-specific co-immobilization of proteins
by: Brabcova, Jana, et al.
Published: (2021) -
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides
by: Pérez-Labrada, Karell, et al.
Published: (2012-04-15) -
Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
by: Pérez-Labrada, Karrel, et al.
Published: (2012-07-12)