Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 13, Pages 2399-2411Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100157
Keywords
Cycloaddition; Click chemistry; Peptidomimetics; Structural Biology; Protein folding
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Funding
- Australian Research Council (ARC)
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The ability to synthesise small peptidomimetics that mimic the secondary structure of proteins is an ever expanding area of research directed at sourcing new medicinal agents and biological probes. A significant current challenge is to mimic protein epitopes under physiological conditions using small peptidomimetics that are easy to prepare. The copper- and ruthenium-catalysed Huisgen cycloaddition reactions provide such a general synthetic method, with the resulting 1,2,3-triazoles being good peptide bond mimics. The ability to prepare both 1,4- and 1,5-substituted 1,2,3-triazoles under these chemically benign conditions provides both linear and bent peptidomimetics. Examples of the use of 1,2,3-triazoles to define the geometry and properties of a peptidomimetic abound. This review highlights such successes but also describes a number of failures in order to guide and inspire future efforts of chemists in this area.
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