188472-87-9Relevant academic research and scientific papers
Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and "unnatural" UDP- and TDP-nucleotide sugars
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, (2008/06/13)
The present invention provides mutant nucleotidylyl-transferases, such as Ep, having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified Ep or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.
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.
