Synthesis of azide-alkyne fragments for ‘click’ chemical applications; formation of oligomers from orthogonally protected trialkylsilyl-propargyl azides and propargyl alcohols |
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| Authors: | Oliver D Montagnat Andrew B Hughes |
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| Institution: | a Department of Chemistry, La Trobe University, Melbourne, Victoria 3086, Australia
b The Walter and Eliza Hall Institute of Medical Research, Structural Biology Division, Medicinal Chemistry Group, 4 Research Avenue, La Trobe University Research and Development Park, Victoria 3086, Australia |
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| Abstract: | A series of orthogonally protected 1,4-disubstituted-1,2,3-triazoles were prepared from the corresponding alkynols and trialkylsilyl-propargyl azides via 1,3-dipolar cycloaddition. These cycloadducts were selectively deprotected and extended in a stepwise fashion via further ‘click’ reactions to form oligomeric peptidomimetic compounds. This methodology gives access to triazole-based peptidomimetics in a controlled fashion and lays the foundation for a fragment-based approach to drug discovery. |
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| Keywords: | &lsquo Click&rsquo chemistry Triazole oligomers 1 3-Dipolar cycloaddition Peptidomimetics |
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