Synthesis of hydrophilic aminooxy linkers and multivalent cores for chemoselective aldehyde/ketone conjugation

Abstract

A series of three linear and two trivalent aminooxy-containing hydrophilic linkers and cores were synthesized. The five molecules contain from one to three aminooxy groups, and all but one contain an ether for enhanced aqueous solubility. These unique and versatile molecules can be utilized in the chemoselective conjugation of aldehyde/ketone-containing molecules, including reducing sugars, under mild aqueous conditions, and give rise to oxime-containing conjugates useful in a wide variety of applications and studies. The value of these aminooxy-based molecules and the ease and speed of preparation of both monovalent and multivalent oxime-linked molecules are demonstrated in two examples using the disaccharide cellobiose; one with a linear linker, and the second with a trivalent core. © 2014 Elsevier Ltd. All rights reserved.