Synthesis of glycopeptides and neoglycoproteins containing the fucosylated linkage region of N-glycoproteins.
N-Glycoproteins fucosylated in the core region occur in tumor membranes and virus envelopes. Partial structures of such N-glycoproteins containing fucosylated chitobiosyl asparagine conjugates were synthesized using the allyloxycarbonyl (Aloc) and the tert-butyl ester protecting groups in the peptide portion. As the alpha-fucosidic bond of the conjugates revealed to be very sensitive to acids when carrying ether-type protecting groups, a method for exchanging the protecting groups of the fucose portion of saccharides was developed. Conjugates containing O-acetyl protected fucose proved to be stable against acids used in glycopeptide syntheses. These methods were applied in the synthesis of a fucosyl chitobiose hexapeptide with the partial sequence of a leukemia virus envelope glycoprotein. The glycopeptide was coupled to bovine serum albumin yielding a neoglycoprotein which contains a glycoconjugate of exactly specified structure.
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Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Germany.
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D000595:Amino Acid Sequence; D001216:Asparagine / Q000737:chemistry; D002240:Carbohydrate Sequence; D004187:Disaccharides; D005643:Fucose / Q000737:chemistry*; D005647:Fucosyltransferases / Q000378:metabolism; D005936:Glucans / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D014764:Viral Proteins / Q000737:chemistry
D004187:Disaccharides; D005936:Glucans; D006020:Glycopeptides; D006023:Glycoproteins; D014764:Viral Proteins; D005643:Fucose; C032438:chitobiose; D001216:Asparagine; D005647:Fucosyltransferases