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Quantitative Determination of Click Reaction in the Presence of Glycine Derivatives and in Dilute Solution
Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
- 1 Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
- 2 Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
- 3 Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
- 4 Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
- 5 Graduate School of Agriculture, Hokkaido University, Sapporo, Japan
International Journal of Organic Chemistry·Volume 02 (2012)·Pages 302–304·Published 3 October 2012·DOI10.4236/ijoc.2012.223041
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Abstract
The click reaction is one of the latest techniques for the functional analysis of bioactive compounds and the analysis makes novel concepts and strategies for medicinal chemistry. N -methylated glycine derivatives have inhibitory activity for the click reaction in direct Cu(I) system because of decrease of Cu(I) concentration. The Cu(I) concentration recovered effectively by sodium ascorbate. Quantitative determination of click reaction at various ligand concentrations revealed that the decrease in reaction yields was observed in a substrate concentration-dependent manner.
KeywordsClick ChemistryQuantitative DeterminationPropargylglycineCu(I)Buffer
- H. C. Kolb, M. G. Finn and K. B. Sharpless, “Click Chemistry: Diverse Chemical Function from a Few Good Reactions,” Angewandte Chemie International Edition, Vol. 40, No. 11, 2001, pp. 2004-2021. doi:10.1002/1521-3773(20010601)40:11 3.0.CO;2-5
- Y. Ogasawara, Y. Murai, Y. Sakihama, Y. Hashidoko and M. Hashimoto, “Quantitative Analysis of Cu(I) Concentration in Click Chemistry—Biotinylation at Side Chain of Propargylglycine Using Click Chemistry under Heating Conditions,” Heterocycles, 2012. doi:10.3987/COM-12-S(N)32
- V. Hong, S. I. Presolski, C. Ma and M. G. Finn, “Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation,” Angewandte Chemie International Edition, Vol. 48, No. 52, 2009, pp. 9879-9883. doi:10.1002/anie.200905087
- A. T. Faizullah and A. Townshend, “Spectrophotometric Determination of Copper by Flow Injection Analysis with an On-Line Reduction Column,” Analytica Chimica Acta, Vol. 172, No. 1, 1985, pp. 291-296. doi:10.1016/S0003-2670(00)82618-5
- W. G. Lewis, F. G. Magallon, V. V. Fokin and M. G. Finn, “Discovery and Characterization of Catalysts for Azide-Alkyne Cycloaddition by Fluorescence Quenching,” Journal of American Chemical Society, Vol. 126, No. 30, 2004, pp. 9152-9153. doi:10.1021/ja048425z
- S. S. Gupta, J. Kuzelka, P. Singh, W. G. Lewis, M. Manchester and M. G. Finn, “Accelerated Bioorthogonal Conjugation: A Practical Method for the Ligation of Diverse Functional Molecules to a Polyvalent Virus Scaffold,” Bioconjugate Chemistry, Vol. 16, No. 6, 2005, pp. 1572-1579. doi:10.1021/bc050147l
- M. Meldal and C. W. Torn?e, “Cu-Catalyzed Azide-Alkyne Cycloaddition,” Chemical Reviews, Vol. 108, No. 8, 2008, pp. 2952-3015. doi:10.1021/cr0783479