In 2018,Steinmeyer, Jeannine; Wagenknecht, Hans-Achim published 《Synthesis of DNA Modified with Boronic Acid: Compatibility to Copper(I)-Catalyzed Azide-Alkyne Cycloaddition》.Bioconjugate Chemistry published the findings.Application In Synthesis of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine The information in the text is summarized as follows:
The postsynthetic and sequence specific ligation chem. of a phenylboronic acid to oligonucleotides using the amide bond formation was worked out. In the first coupling experiments with 4 carboxyphenylboronic acid a 5′-hexylamino-modified oligonucleotide was used in order to evaluate and to optimize the reaction conditions. This postsynthetic modification works best in the presence of TBTU and triethanolamine and in a degassed DMF/carbonate buffer solvent mixture The successful attachment of the boronic acid was evidenced by HPLC separation from phenol side products and clear identification via MALDI-TOF mass spectrometry as citric acid derivative This postsynthetic chem. was further combined with the established Cu(I)-catalyzed azide-alkyne cycloaddition chem. to allow the first orthogonal and postsynthetic incorporation of both the phenylboronic acid moiety and two different cyanine-styryl dyes. Due to the undesired reactivity of boronic acids by the presence of copper salts, the dye azides were firstly attached to the pre-synthesized oligonucleotides using the Cu(I)-catalyzed cycloaddition at the 2′-position of a propargylated uridine. After careful removal of all copper contaminants the amide bond with the 4-carboxyphenylboronic acid at the propylamine linker of a 7-deaza-2′-deoxyadenosine as anchor point was formed. These doubly modified oligonucleotides were characterized by their optical properties to elucidate the influence of the phenylboronic acid. The latter modification has only little influence on the fluorescence of the applied dyes. In conclusion, this postsynthetic and orthogonal chem. opens the way to a broad variety of applications, in particular saccharide detection based on fluorescent DNA aptamers.Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8Application In Synthesis of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine) was used in this study.
Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8) can stabilizes Cu(I) towards disproportionation and oxidation thus enhancing its catalytic effect in the azide-acetylene cycloaddition.Application In Synthesis of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)aminePolytriazolylamines were synthesized by the copper(I)-catalyzed ligation of azides and alkynes.
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics