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Water-soluble NHC-Cu catalysts : applications in click chemistry, bioconjugation and mechanistic analysis

(2014) ORGANIC & BIOMOLECULAR CHEMISTRY. 12(46). p.9350-9356
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Abstract
Copper(I)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as “click” reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materials science and combinatorial chemistry. Here we report a new series of water-soluble catalysts based on N-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonate group. The complexes show superior activity towards CuAAC reactions and display a high versatility, enabling the production of triazoles with different substitution patterns. Additionally, successful application of these complexes in bioconjugation using unprotected peptides acting as DNA binding domains was achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations.
Keywords
NH-1_2_3-TRIAZOLES, 1_2_3-TRIAZOLES, 1H-1_2_3-TRIAZOLES, DNA-BINDING, PROTEIN OXIDATION, SODIUM-AZIDE, OLEFIN METATHESIS CATALYSTS, AZIDE-ALKYNE CYCLOADDITION, PEPTIDE, DIMER

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Citation

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MLA
Díaz Velázquez, Heriberto, et al. “Water-Soluble NHC-Cu Catalysts : Applications in Click Chemistry, Bioconjugation and Mechanistic Analysis.” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 12, no. 46, 2014, pp. 9350–56.
APA
Díaz Velázquez, H., Ruiz Garcia, Y., Vandichel, M., Madder, A., & Verpoort, F. (2014). Water-soluble NHC-Cu catalysts : applications in click chemistry, bioconjugation and mechanistic analysis. ORGANIC & BIOMOLECULAR CHEMISTRY, 12(46), 9350–9356.
Chicago author-date
Díaz Velázquez, Heriberto, Yara Ruiz Garcia, Matthias Vandichel, Annemieke Madder, and Francis Verpoort. 2014. “Water-Soluble NHC-Cu Catalysts : Applications in Click Chemistry, Bioconjugation and Mechanistic Analysis.” ORGANIC & BIOMOLECULAR CHEMISTRY 12 (46): 9350–56.
Chicago author-date (all authors)
Díaz Velázquez, Heriberto, Yara Ruiz Garcia, Matthias Vandichel, Annemieke Madder, and Francis Verpoort. 2014. “Water-Soluble NHC-Cu Catalysts : Applications in Click Chemistry, Bioconjugation and Mechanistic Analysis.” ORGANIC & BIOMOLECULAR CHEMISTRY 12 (46): 9350–9356.
Vancouver
1.
Díaz Velázquez H, Ruiz Garcia Y, Vandichel M, Madder A, Verpoort F. Water-soluble NHC-Cu catalysts : applications in click chemistry, bioconjugation and mechanistic analysis. ORGANIC & BIOMOLECULAR CHEMISTRY. 2014;12(46):9350–6.
IEEE
[1]
H. Díaz Velázquez, Y. Ruiz Garcia, M. Vandichel, A. Madder, and F. Verpoort, “Water-soluble NHC-Cu catalysts : applications in click chemistry, bioconjugation and mechanistic analysis,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 12, no. 46, pp. 9350–9356, 2014.
@article{5758766,
  abstract     = {Copper(I)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as “click” reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materials science and combinatorial chemistry. Here we report a new series of water-soluble catalysts based on N-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonate group. The complexes show superior activity towards CuAAC reactions and display a high versatility, enabling the production of triazoles with different substitution patterns. Additionally, successful application of these complexes in bioconjugation using unprotected peptides acting as DNA binding domains was achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations.},
  author       = {Díaz Velázquez, Heriberto and Ruiz Garcia, Yara and Vandichel, Matthias and Madder, Annemieke and Verpoort, Francis},
  issn         = {1477-0520},
  journal      = {ORGANIC & BIOMOLECULAR CHEMISTRY},
  keywords     = {NH-1_2_3-TRIAZOLES,1_2_3-TRIAZOLES,1H-1_2_3-TRIAZOLES,DNA-BINDING,PROTEIN OXIDATION,SODIUM-AZIDE,OLEFIN METATHESIS CATALYSTS,AZIDE-ALKYNE CYCLOADDITION,PEPTIDE,DIMER},
  language     = {eng},
  number       = {46},
  pages        = {9350--9356},
  title        = {Water-soluble NHC-Cu catalysts : applications in click chemistry, bioconjugation and mechanistic analysis},
  url          = {http://dx.doi.org/10.1039/C4OB01350F},
  volume       = {12},
  year         = {2014},
}

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