PMID: 11906266Mar 22, 2002Paper

Immobilization of pectin fragments on solid supports: novel coupling by thiazolidine formation

Bioconjugate Chemistry
Fanny GuillaumieKnud J Jensen

Abstract

As a prerequisite to solid-phase and sequence analyses and for the study of the fine structure of pectin, we have developed oriented and chemoselective methodologies to couple model pectin fragments onto a solid support. Polyethylene glycol polyacrylamide (PEGA) resins were selected due to their excellent swelling properties in a wide range of solvents, including water, and their easy accessibility to enzymes. Following appropriate derivatization of amino-terminated PEGA resins, oligomers of alpha-D-galacturonic acid (GalA), up to the trimer, were anchored to the support through their reducing end. In addition to reductive amination, the strategies included the formation of an oxime bond, a glycosyl hydrazide, and a pyroglutamyl ring. Further, we developed a new immobilization approach based on the formation of a thiazolidine ring. All methods proved efficient and did not require modification of the GalA oligomers prior to coupling. In addition, very mild conditions and few steps for derivatization of the support were required. Immobilization by thiazolidine ring and oxime bond formation were the preferred methods, given the stability of the linkages formed, their compatibility with aqueous solvents, the few number of steps req...Continue Reading

Citations

Oct 12, 2010·Bioconjugate Chemistry·Avijit Kumar AdakAlexander Wei
Oct 27, 2010·Journal of Medicinal Chemistry·Randal D Goff, Jon S Thorson
Sep 20, 2008·Chemical Communications : Chem Comm·Nicolas LaurentSabine L Flitsch
Aug 2, 2008·Glycoconjugate Journal·Carmen Jiménez-CastellsRicardo Gutiérrez-Gallego
Jul 29, 2004·Biotechnology and Bioengineering·Anders Heebøll-NielsenOwen R T Thomas
Jul 1, 2005·Protein Science : a Publication of the Protein Society·Marcus JägerShimon Weiss
Oct 24, 2012·Proteomics. Clinical Applications·Shuang Yang, Hui Zhang
Sep 6, 2005·Chembiochem : a European Journal of Chemical Biology·Miquel Vila-PerellóDavid Andreu
Jan 10, 2017·Chembiochem : a European Journal of Chemical Biology·Klaus VilladsenMikkel B Thygesen
Jun 5, 2004·The World Journal of Biological Psychiatry : the Official Journal of the World Federation of Societies of Biological Psychiatry·Richard Noll
Nov 11, 2020·Chemistry : a European Journal·Karin MannerstedtKnud J Jensen
Feb 6, 2010·The Journal of Organic Chemistry·Mikkel B ThygesenKnud J Jensen
May 24, 2006·Carbohydrate Research·Kim LarsenKnud J Jensen

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