Diversity Oriented Combinatorial Synthesis of Multivalent Glycomimetics Through a Multicomponent Domino Process
| Autor: | Alessandro Volonterio, Aurora Sganappa, Monica Sani, Maria Cristina Bellucci |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization multicomponent reaction Primary (chemistry) Magnetic Resonance Spectroscopy Molecular Structure Chemistry Neomycin diversity oriented synthesis General Chemistry General Medicine Combinatorial synthesis multivalent glycomimetics High yielding Combinatorial chemistry Cascade reaction domino reaction Biomimetics Organic chemistry Combinatorial Chemistry Techniques Domino process Linker Glycoconjugates combinatorial chemistry |
| Zdroj: | ACS combinatorial science 16 (2014): 711–720. doi:10.1021/co5001184 info:cnr-pdr/source/autori:Bellucci, Maria Cristina; Sani, Monica; Sganappa, Aurora; Volonterio, Alessandro/titolo:Diversity Oriented Combinatorial Synthesis of Multivalent Glycomimetics Through a Multicomponent Domino Process/doi:10.1021%2Fco5001184/rivista:ACS combinatorial science (Print)/anno:2014/pagina_da:711/pagina_a:720/intervallo_pagine:711–720/volume:16 |
| DOI: | 10.1021/co5001184 |
| Popis: | Both multicomponent reactions and diversity oriented synthesis are indispensable tools for the modern medicinal chemist. However, their employment for the synthesis of multivalent glycomimetics has not been exploited so far although the importance that such compounds play in exploring multivalency on glycoside inhibition. Herein, we report the combinatorial synthesis of diversity oriented hetero di- and trivalent glycomimetics through a multicomponent domino process. The process is high yielding and very general, working efficiently with easily accessible sugar starting materials such as glycosylamines, glycosylazides, and glycosylisothiocyanates, having the reactive functional groups tethered either directly to the anomeric carbon, through a suitable linker, or to the primary 6 position of hexoses (or 5 position of pentoses), leading, in the latter case, to glycomimetics with artificial enzymatically stable backbone. The process has been also exploited for the multicomponent synthesis of aminoglycoside (neomycin) conjugates. |
| Databáze: | OpenAIRE |
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