15451-80-6Relevant academic research and scientific papers
Synthesis of Hexp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3 probes for exploration of the substrate specificity of glycosyltransferases
Van Dorst, Johannes A.L.M.,Van Heusden, Cornelis J.,Tikkanen, Jaana M.,Kamerling, Johannis P.,Vliegenthart, Johannes F.G.
, p. 209 - 227 (2007/10/03)
Seven analogues of the trisaccharide β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3 have been synthesized as potential substrates for glycosyltransferases involved in the chain-termination of N-acetyllactosamine-type N-glycans. These compounds include: 3-O-methyl-β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, 3-deoxy-β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, 3 -deoxy-3-fluoro-β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, 3-amino-3-deoxy-β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, β-D-Gulp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, β-L-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3, and α-L-Altp-(1 → 4)-β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → O)(CH2)7CH3. All trisaccharides were obtained by condensation of suitably modified glycosyl donors based on imidates or thioglycosides with the same disaccharide acceptor, octyl 3,4,6-tri-O-benzyl-2-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido- β-D -glucopyranosyl)-α-D-mannopyranoside, followed by deprotection.
