“Clickable” Agarose for Affinity Chromatography

Abstract

Successful purification of biological molecules by affinity chromatography requires the attachment of desired ligands to biocompatible chromatographic supports. The Cu(I)-catalyzed cycloaddition of azides and alkynes-the premier example of "click chemistry"-is an efficient way to make covalent connections among diverse molecules and materials. Both azide and alkyne units are highly selective in their reactivity, being inert to most chemical functionalities and stable to wide ranges of solvent, temperature, and pH. We show that agarose beads bearing alkyne and azide groups can be easily made and are practical precursors to functionalized agarose materials for affinity chromatography.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Finn et al [356] described the click functionalization of a commercial porous agarose resin for affinity chromatography. In two parallel experiments, amino agarose beads were treated with azide and alkyne carrying activated esters respectively (Scheme 3).…”

1,3‐Dipolare Cycloaddition von Aziden und Alkinen: eine universelle Ligationsmethode in den Polymer‐ und Materialwissenschaften

“…[46] Die Azid/Alkin-Ligation wurde auch zur Synthese von Volumenmaterialien angewendet. [17,18,20,23,82] Die Arbeitsgruppen um Hawker und Hilbon beschrieben die Synthese von Poly(ethylenglycol)-oder Poly(vinylalkohol)-haltigen Hydrogelen, die über Triazolringe vernetzt sind. [17,82] ¾hnli-che Synthesestrategien wurden zur Anknüpfung von Liganden an Gelperlen angewendet, die in der Affinitätschroma-tographie und der Elektrophorese Verwendung finden.…”

“…[17,82] ¾hnli-che Synthesestrategien wurden zur Anknüpfung von Liganden an Gelperlen angewendet, die in der Affinitätschroma-tographie und der Elektrophorese Verwendung finden. [18,23] Abbildung 2. Oben: Herstellung von Polystyrol-modifizierten einwandigen Kohlenstoff-Nanoröhren durch Klick-Chemie.…”

Synthesis of Glyco‐Silicas by Cu(I)‐Catalyzed “Click‐Chemistry” and their Applications in Affinity Chromatography

“…All these outstanding features have found huge applications in biomedicinal science, organic synthesis and materials science. [17] In particular, novel functionalized supports based in silica [18] and agarose [19] as well in the covalent ligation of carbohydrates probes to a solid surface [20] for the development of glycoarrays, [21] carbohydrate-containing quantum-dots [22] and sugars-SAMs [23] have been efficiently prepared by this methodology.…”