Dataset Information

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 is demonstrated in two examples using the disaccharide cellobiose; one with a linear linker, and the second with a trivalent core.

SUBMITTER: McReynolds KD

PROVIDER: S-EPMC4220302 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis of Hydrophilic Aminooxy Linkers and Multivalent Cores for Chemoselective Aldehyde/Ketone Conjugation.

McReynolds Katherine D KD Dimas Dustin D Le Hoang H

Tetrahedron letters 20140401 14

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 ap ...[more]

PMID: 25382876

Similar Datasets

Project description:Surface-initiated activators regenerated by electron transfer atom transfer radical polymerization (ARGET ATRP) is used to polymerize a cis-diol-functional methacrylic monomer (herein denoted GEO5MA) from planar silicon wafers. Ellipsometry studies indicated dry brush thicknesses ranging from 40 to 120 nm. The hydrophilic PGEO5MA brush is then selectively oxidized using sodium periodate to produce an aldehyde-functional hydrophilic PAGEO5MA brush. This post-polymerization modification strategy provides access to significantly thicker brushes compared to those obtained by surface-initiated ARGET ATRP of the corresponding aldehyde-functional methacrylic monomer (AGEO5MA). The much slower brush growth achieved in the latter case is attributed to the relatively low aqueous solubility of the AGEO5MA monomer. X-ray photoelectron spectroscopy (XPS) analysis confirmed that precursor PGEO5MA brushes were essentially fully oxidized to the corresponding PAGEO5MA brushes within 30 min of exposure to a dilute aqueous solution of sodium periodate at 22 °C. PAGEO5MA brushes were then functionalized via Schiff base chemistry using an amino acid (histidine), followed by reductive amination with sodium cyanoborohydride. Subsequent XPS analysis indicated that the mean degree of histidine functionalization achieved under optimized conditions was approximately 81%. Moreover, an XPS depth profiling experiment confirmed that the histidine groups were uniformly distributed throughout the brush layer. Surface ζ potential measurements indicated a significant change in the electrophoretic behavior of the zwitterionic histidine-functionalized brush relative to that of the non-ionic PGEO5MA precursor brush. The former brush exhibited cationic character at low pH and anionic character at high pH, with an isoelectric point being observed at around pH 7. Finally, quartz crystal microbalance studies indicated minimal adsorption of a model globular protein (BSA) on a PGEO5MA brush-coated substrate, whereas strong protein adsorption via Schiff base chemistry occurred on a PAGEO5MA brush-coated substrate.

Dataset Information

Synthesis of Hydrophilic Aminooxy Linkers and Multivalent Cores for Chemoselective Aldehyde/Ketone Conjugation.

Publications

Synthesis of Hydrophilic Aminooxy Linkers and Multivalent Cores for Chemoselective Aldehyde/Ketone Conjugation.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets