Solid-phase synthesis of a fucosylated glycopeptide of human factor IX with a fucose-α-(1→O)-serine linkage
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 3017-3022
- https://doi.org/10.1039/p19950003017
Abstract
The chemical synthesis of a glycopeptide with L-fucose directly linked to the hydroxy group of L-serine is reported. Two building blocks containing a protected and an unprotected fucose residue α-glycosidically linked to Nα-Fmoc-Ser-OH were prepared and used in the synthesis of a glycopeptide fragment of the EGF domain of Human Factor IX 55–65. It was demonstrated that both building blocks were completely compatible with the standard Fmoc-based solid-phase peptide synthesis protocol and furthermore that OH protection of the carbohydrate is necessary only during the final acid treatment for cleavage of the glycopeptide from the resin.Keywords
This publication has 15 references indexed in Scilit:
- Synthesis, characterization and biocompatibility of PEGA resinsJournal of Peptide Science, 1995
- Synthesis of glycopeptides and neoglycoproteins containing the fucosylated linkage region of N-glycoproteinsBioorganic & Medicinal Chemistry, 1994
- Protein glycosylationEuropean Journal of Biochemistry, 1993
- Identification and structural analysis of the tetrasaccharide NeuAc.alpha.(2.fwdarw.6)Gal.beta.(1.fwdarw.4)GlcNAc.beta.(1.fwdarw.3)Fuc.alpha.1.fwdarw.O-linked to serine 61 of human factor IXBiochemistry, 1993
- Tissue plasminogen activator has an O-linked fucose attached to threonine-61 in the epidermal growth factor domainBiochemistry, 1991
- New coupling reagents in peptide chemistryTetrahedron Letters, 1989
- Synthetic, conformational, and immunochemical studies of modified Lewis b and Y human blood-group determinants to serve as probes for the combining site of the lectin IV of Griffonia simplicifoliaCarbohydrate Research, 1988
- Peptide synthesis. Part 13. Feedback control in solid phase synthesis. Use of fluorenylmethoxycarbonyl amino acid 3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl esters in a fully automated systemJournal of the Chemical Society, Perkin Transactions 1, 1988
- Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharidesJournal of the American Chemical Society, 1975
- Studies on the Koenigs-Knorr reaction : Part II. Synthesis of an α-L-linked disaccharide from tri-O-benzyl-α-L-fucopyranosyl bromideCarbohydrate Research, 1971