Chemistry
Document Type
Article
Abstract
Copper-catalyzed azide–alkyne cycloaddition click (CuAAC) reaction is widely used to synthesize drug candidates and other biomolecule classes. Homogeneous catalysts, which consist of copper coordinated to a ligand framework, have been optimized for high yield and specificity of the CuAAC reaction, but CuAAC reaction with these catalysts requires the addition of a reducing agent and basic conditions, which can complicate some of the desired syntheses. Additionally, removing copper from the synthesized CuAAC-containing biomolecule is necessary for biological applications but inconvenient and requires additional purification steps. We describe here the design and synthesis of a PNN-type pincer ligand complex with copper (I) that stabilizes the copper (I) and, therefore, can act as a CuAAC catalyst without a reducing agent and base under physiologically relevant conditions. This complex was immobilized on two types of resin, and one of the immobilized catalyst forms worked well under aqueous physiological conditions. Minimal copper leaching was observed from the immobilized catalyst, which allowed its use in multiple reaction cycles without the addition of any reducing agent or base and without recharging with copper ion. The mechanism of the catalytic cycle was rationalized by density functional theory (DFT). This catalyst’s utility was demonstrated by synthesizing coumarin derivatives of small molecules such as ferrocene and sugar. © 2024 by the authors.
Publication Title
Molecules
Publication Date
5-2024
Volume
29
Issue
9
ISSN
1420-3049
DOI
10.3390/molecules29092148
Keywords
Cu(I) complex, deuterated solvent effect, heterogeneous catalysis, PNN ligand, “click”
Repository Citation
Kandler, Rene; Benaragama, Yomal; Bera, Manoranjan; Wang, Caroline; Samiha, Rasheda Aktar; Sameera, W.M.C.; Das, Samir; and Nag, Arundhati, "Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules" (2024). Chemistry. 34.
https://commons.clarku.edu/chemistry/34
Cross Post Location
Student Publications
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Copyright Conditions
Published source must be acknowledged with citation: Kandler, R., Benaragama, Y., Bera, M., Wang, C., Samiha, R. A., Sameera, W. M. C., ... & Nag, A. (2024). Development of Novel Immobilized Copper–Ligand Complex for Click Chemistry of Biomolecules. Molecules, 29(9), 2148.
