'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Novel analogs of spirostan saponins in which the glycosidic bond has been replaced by a triazole linkage are described.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.

Bibliographic Details

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
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