Reliable and Efficient Procedures for the Conjugation of Biomolecules through Huisgen Azide–Alkyne Cycloadditions

Abstract

The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) has been established as a powerful coupling technology for the conjugation of proteins, nucleic acids, and polysaccharides. Nevertheless, several shortcomings related to the presence of Cu, mainly oxidative degradation by reactive oxygen species and sample contamination by Cu, have been pointed out. This Minireview discusses key aspects found in the development of the efficient and benign functionalization of biomacromolecules through CuAAC, as well as the Cu-free strain-promoted azide-alkyne cycloaddition (SPAAC).

Multicomponent Click Synthesis of New 1,2,3-Triazole Derivatives of Pyrimidine Nucleobases: Promising Acidic Corrosion Inhibitors for Steel

“…The procedure described above (using the same quantities of Cu(OAc) 2 ·H 2 O, 1,10-phenanthroline monohydrate, sodium L-ascorbate) was followed to obtain compound 8, employing 3 (60 mg, 0. (9). The procedure described above was followed to obtain compound 9, employing Cu(OAc) 2 (10).…”

“…Nowadays, the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC, also known as the copper(I)-catalyzed Huisgen-Meldal-Sharpless cycloaddition) is the most widely used method for the synthesis of 1,4-disubstituted 1,2,3-triazoles from a wide range of organic azides and terminal alkynes [3][4][5][6][7]. Moreover, this process allows for the assembly of complex molecules, thus generating new unknown structures with an added potential biological and engineering value [8][9][10]. Monopropargyl pyrimidine nucleobases (uracil and thymine) are versatile building blocks for the synthesis of biologically relevant 1,2,3-triazoles [11].…”

Unnatural Amino Acid Mediated Protein Bioorthogonal Labeling

“…这其中, 由一价铜离子催化的 叠氮与炔基的环加成反应(CuAAC) [5] , 也就是我们通常 说的"点击"化学反应("Click" Chemistry), 已经成为 最为人所熟知的生物正交反应之一. 该反应已经在从生 物材料制备到活细胞成像等多个领域获得了广泛的应 用 [6] . 然而, 一价铜离子所产生的细胞毒性是目前阻碍 该反应在生命体系中具有普适性应用的屏障 [7] .…”

Synthesis and catalytic applications of C3-symmetric tris(triazolyl)methanol ligands and derivatives

“…This last feature has enabled the conjugation of several biomacromolecules −encompassing proteins, nucleic acids, lipids and glycans− with biophysical probes delivering biocompatible systems for both in vitro and in vivo studies. 10 Concerning the preparation of triazole-based molecular architectures, CuAAC reactions have exerted a tremendous influence in the materials chemistry arena. Thus, the reaction has provided access to well-defined, complex polymeric materials (linear polymers, surfaces, star-shaped polymers), 11 functional polymers (stimuli-responsive hydrogels) 12 and also dendrimers.…”