Enzymatic synthesis of site-specifically (alpha 1-3)-fucosylated polylactosamines containing either a sialyl Lewis (x), a VIM-2, or a sialylated and internally difucosylated sequence.
By using two different reaction pathways, we generated enzymatically three sialylated and site-specifically alpha 1-3-fucosylated polylactosamines. Two of these are isomeric hexasaccharides Neu5Ac(alpha 2-3)Gal(beta 1-4)GlcNAc(beta 1-3)Gal(beta 1-4)[Fuc(alpha 1-3)] GlcNAc and Neu5Ac(alpha 2-3)Gal(beta 1-4)[Fuc(alpha 1-3)]GlcNAc(beta 1-3)Gal(beta 1-4) GlcNAc, containing epitopes that correspond to VIM-2 and sialyl Lewis (x), respectively. The third one, nonasaccharide Neu5Ac(alpha 2-3)Gal(beta 1-4)GlcNAc(beta 1-3)Gal(beta 1-4)[Fuc(alpha 1-3)] GlcNAc(beta 1-3)Gal(beta 1-4)[Fuc(alpha 1-3)]GlcNAc, is a sialylated and internally difucosylated derivative of a trimeric N-acetyllactosamine. All three oligosaccharides have one fucose-free N-acetyllactosaminyl unit and can be used as acceptors for recombinant alpha 1-3-fucosyltransferases in determining the biosynthesis pathways leading to polyfucosylated selectin ligands.
Räbinä
J
J
Institute of Biotechnology, University of Helsinki, Finland.
Natunen
J
J
Niemelä
R
R
Salminen
H
H
Ilves
K
K
Aitio
O
O
Maaheimo
H
H
Helin
J
J
Renkonen
O
O
D000606:Amino Sugars / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D005643:Fucose / Q000737:chemistry; D016695:Glycosyltransferases / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D019158:N-Acetylneuraminic Acid / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis*; D019087:Selectins / Q000378:metabolism; D000080506:Sialyl Lewis X Antigen; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
D000606:Amino Sugars; D009844:Oligosaccharides; D011134:Polysaccharides; D019087:Selectins; D000080506:Sialyl Lewis X Antigen; C070946:VIM-2 determinant; C066929:polylactosamine; D005643:Fucose; D016695:Glycosyltransferases; D001619:beta-N-Acetylhexosaminidases; D019158:N-Acetylneuraminic Acid