Synthesis of heterobifunctional poly(ethylene glycol) with a reducing monosaccharide residue at one end.
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.
Nakamura
T
T
Department of Materials Science and Technology, Science University of Tokyo, Noda, Japan.
Nagasaki
Y
Y
Kataoka
K
K
D000838:Anions; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003432:Cross-Linking Reagents; D005027:Ethylene Oxide / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry
D000838:Anions; D003432:Cross-Linking Reagents; D009005:Monosaccharides; D011108:Polymers; D011092:Polyethylene Glycols; D005947:Glucose; D005027:Ethylene Oxide; D005690:Galactose