Highly regioselective synthesis of a 3-O-sulfonated arabino Lewis(a) asparagine building block suitable for glycopeptide synthesis.
Using the stannylene method, the trisaccharide 2-acetamido-3-O-[6-O-benzyl-beta-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-beta-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide was regioselectively sulfonated and, after reduction of the anomeric azide, coupled to Fmoc alpha-allyl aspartate. After Pd(0)-catalyzed deallylation, the sulfatyl Lewis(a) asparagine building block was obtained, suitable for solid-phase glycopeptide synthesis applying the fluoride labile PTMSEL linker system.
Rösch
Alexander
A
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
Kunz
Horst
H
D001216:Asparagine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D006020:Glycopeptides / Q000138:chemical synthesis; D006031:Glycosylation; D007983:Lewis Blood Group Antigens; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D006020:Glycopeptides; D007983:Lewis Blood Group Antigens; C494219:Lewis a oligosaccharide; D009842:Oligopeptides; D009844:Oligosaccharides; D001216:Asparagine