Expedient synthesis of a series of N-acetyllactosamines.
A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-D-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced.
McAuliffe
J C
JC
The Burnham Institute, San Diego, CA 92122, USA.
Fukuda
M
M
Hindsgaul
O
O
D000606:Amino Sugars / Q000737:chemistry*; D002240:Carbohydrate Sequence; D016695:Glycosyltransferases / Q000378:metabolism; D007700:Kinetics; D008362:Mannosides / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000378:metabolism; D013379:Substrate Specificity
D000606:Amino Sugars; D008362:Mannosides; D009844:Oligosaccharides; C000458:N-acetyllactosamine; D016695:Glycosyltransferases