Synthesis of heterobifunctional poly(ethylene glycol) with a reducing monosaccharide residue at one end

Bioconjugate Chemistry
T NakamuraKazunori Kataoka

Abstract

A new synthetic method for a heterobifunctional poly(ethylene glycol) (PEG) having a monosaccharide moiety at one end was created. PEG with a reducing monosaccharide residue at the alpha-end, which is linked to a defined position of the sugar molecule, could be prepared via the anionic polymerization of ethylene oxide (EO) initiated with a potassium alkolate of a protected monosaccharide such as 1,2;5,6-di-O-isopropylidene-D-glucofuranose (DIGL), 1,2;3,4-di-O-isopropylidene-D-galactopyranose (DIGA), and 1,2-O-isopropylidene-3,5-O-benzylidene-D-glucofuranose (IBGL). The resulting PEGs possess the corresponding sugar molecule at the alpha-chain end and a hydroxyl group at the omega-chain end. The omega-chain end could be converted to several functional groups such as allyl, amino, and hydroxycarbonyl groups in high yield. Such heterobifunctional PEGs possessing a reducing monosaccharide residue at the alpha-end are one of the promising tools for bioconjugate chemistries.

Citations

Mar 17, 2001·Advanced Drug Delivery Reviews·K KataokaY Nagasaki
Mar 12, 2003·Advanced Drug Delivery Reviews·Hidenori OtsukaKazunori Kataoka
Mar 13, 2012·Acta Biomaterialia·Xiao-Bing XiongAfsaneh Lavasanifar
Nov 18, 2005·Journal of Controlled Release : Official Journal of the Controlled Release Society·Geneviève GaucherJean-Christophe Leroux
Aug 13, 2011·Biomacromolecules·Sumati BhatiaAshok K Prasad
Mar 1, 2018·Macromolecular Bioscience·Tobias C MajdanskiMichael Gottschaldt
Dec 7, 2018·Journal of Materials Science. Materials in Medicine·Man TheerasilpNorased Nasongkla
Jul 30, 2019·Advanced Materials·Peng MiKazunori Kataoka
Jan 15, 2019·Journal of Controlled Release : Official Journal of the Controlled Release Society·Yu YiKazunori Kataoka
Feb 6, 2008·Biomacromolecules·M L VadalaJ S Riffle
Mar 12, 2009·Bioconjugate Chemistry·Zhongyu Li, Ying Chau
Sep 2, 2000·The Journal of Organic Chemistry·N N Reed, K D Janda

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