Abstract
Iodo-1,2,3-triazoles are of considerable interest for chemical and biomedical applications. However, current synthetic methods for preparing iodo-1,2,3-triazoles cannot easily be applied to the direct modification of bioactive molecules in water. Through the combination of water-compatible oxidative iodination and the copper-catalyzed alkyne-azide cycloaddition reaction, a novel copper-catalyzed aqueous multicomponent synthetic method for the preparation of 5-iodo-1,2,3-triazoles has been developed. The method is highly effective and selective for substrates including biologically relevant compounds with nucleoside, sugar, and amino acid moieties. Based on this aqueous tandem reaction, a direct single-step multicomponent dual modification of peptide is developed from readily available starting materials. Furthermore, the method could also be applied to concise and fast multicomponent radioactive 125 I labeling from an aqueous solution of commercially available sodium 125 iodide as a starting material.
Original language | English (US) |
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Pages (from-to) | 1166-1172 |
Number of pages | 7 |
Journal | Chemistry - A European Journal |
Volume | 23 |
Issue number | 5 |
DOIs | |
State | Published - Jan 23 2017 |
Keywords
- Alkynes/chemistry
- Azides/chemistry
- Catalysis
- Copper/chemistry
- Cycloaddition Reaction
- Iodine Radioisotopes/chemistry
- Isotope Labeling
- Peptides/chemistry
- Triazoles/chemical synthesis
- Water/chemistry