Sulfated ligands for the copper(I)-catalyzed azide-alkyne cycloaddition

Wei Wang, Senglian Hong, Andrew Tran, Hao Jiang, Rebecca Triano, Yi Liu, Xing Chen, Peng Wu

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), the prototypical reaction of click chemistry, is accelerated by tris(triazolylmethyl)amine-based ligands. Herein, we compare two new ligands in this family-3-[4-({bis[(1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)- 1H-1,2,3-triazol-1-yl]propanol (BTTP) and the corresponding sulfated ligand 3-[4-({bis[(1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)-1H-1,2, 3-triazol-1-yl]propyl hydrogen sulfate (BTTPS)-for three bioconjugation applications: 1)labeling of alkyne-tagged glycoproteins in crude cell lysates, 2)labeling of alkyne- or azide-tagged glycoproteins on the surface of live mammalian cells, and 3)labeling of azides in surface proteins of live Escherichia coli. Although BTTPS exhibits faster kinetics than BTTP in accelerating the CuAAC reaction in in vitro kinetic measurements, its labeling efficiency is slightly lower than BTTP in modifying biomolecules with a significant amount of negative charges due to electrostatic repulsion. Nevertheless, the negative charge conferred by the sulfate at physiological conditions significantly reduced the cellular internalization of the coordinated copper(I), thus making BTTPS-CuI a better choice for live-cell labeling.

Original languageEnglish (US)
Pages (from-to)2796-2802
Number of pages7
JournalChemistry - An Asian Journal
Volume6
Issue number10
DOIs
StatePublished - Oct 4 2011

Keywords

  • bioconjugation
  • click chemistry
  • copper
  • cycloaddition
  • glycoconjugates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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    Wang, W., Hong, S., Tran, A., Jiang, H., Triano, R., Liu, Y., Chen, X., & Wu, P. (2011). Sulfated ligands for the copper(I)-catalyzed azide-alkyne cycloaddition. Chemistry - An Asian Journal, 6(10), 2796-2802. https://doi.org/10.1002/asia.201100385