Multicomponent Aqueous Synthesis of Iodo-1,2,3-triazoles: Single-Step Models for Dual Modification of Free Peptide and Radioactive Iodo Labeling

Lingjun Li, Shengqiang Ding, Yanping Yang, Anlian Zhu, Xincui Fan, Mengchao Cui, Changpo Chen, Guisheng Zhang

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)1166-1172
Number of pages7
JournalChemistry - A European Journal
Volume23
Issue number5
DOIs
StatePublished - 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

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