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Title

'Click' synthesis of triazole-based spirostan saponin analogs

AuthorsPérez-Labrada, Karell; Brouard, Ignacio ; Morera, Cercis; Estévez, Francisco; Bermejo, Jaime ; Rivera, Daniel G.
KeywordsSteroids
Carbohydrates
Saponins
Click chemistry
Cycloaddition reactions
Issue Date7-Oct-2011
PublisherElsevier
CitationTetrahedron 67(40): 7713-7727 (2011)
AbstractNovel analogs of spirostan saponins in which the glycosidic bond has been replaced by a triazole linkage are described.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.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2011.08.003
URIhttp://hdl.handle.net/10261/199643
DOI10.1016/j.tet.2011.08.003
Identifiersdoi: 10.1016/j.tet.2011.08.003
issn: 0040-4020
Appears in Collections:(IPNA) Artículos
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