Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants.
Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of α-fucoses is demonstrated for H-type I and II; α(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Heung Sik
HS
Hahm
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Chien-Fu
CF
Liang
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Chian-Hui
CH
Lai
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Richard J
RJ
Fair
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Frank
F
Schuhmacher
Department of Biomolecular Systems, Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.
Peter H
PH
Seeberger
D001789:Blood Group Antigens / Q000737:chemistry*; D002625:Chemistry, Organic; D002851:Chromatography, High Pressure Liquid; D000939:Epitopes / Q000737:chemistry; D005643:Fucose / Q000737:chemistry; D006031:Glycosylation; D006801:Humans; D009844:Oligosaccharides / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry
D001789:Blood Group Antigens; D000939:Epitopes; D009844:Oligosaccharides; D011134:Polysaccharides; D013865:Thioglycosides; D005643:Fucose