Reaction participants Show >> << Hide
- Name help_outline a β-D-galactosyl-(1→4)-N-acetyl-β-D-6-sulfooxy-glucosaminyl derivative Identifier CHEBI:149663 Charge -1 Formula C14H23NO14SR SMILEShelp_outline O[C@@H]1[C@H]([C@H](O[C@@H]2[C@H](O[C@@H](O*)[C@@H]([C@H]2O)NC(C)=O)COS([O-])(=O)=O)O[C@@H]([C@@H]1O)CO)O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CMP-N-acetyl-β-neuraminate Identifier CHEBI:57812 (Beilstein: 5899715) help_outline Charge -2 Formula C20H29N4O16P InChIKeyhelp_outline TXCIAUNLDRJGJZ-BILDWYJOSA-L SMILEShelp_outline [H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(N)nc1=O)C([O-])=O)[C@H](O)[C@H](O)CO 2D coordinates Mol file for the small molecule Search links Involved in 106 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an α-Neu5Ac-(2→6)-β-D-Gal-(1→4)-β-D-GlcNAc6S derivative Identifier CHEBI:232694 Charge -2 Formula C25H39N2O22SR SMILEShelp_outline O([C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COS([O-])(=O)=O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO[C@]3(O[C@@]([C@@H]([C@H](C3)O)NC(C)=O)([H])[C@@H]([C@@H](CO)O)O)C([O-])=O)O)O)O)O)NC(=O)C)* 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CMP Identifier CHEBI:60377 Charge -2 Formula C9H12N3O8P InChIKeyhelp_outline IERHLVCPSMICTF-XVFCMESISA-L SMILEShelp_outline Nc1ccn([C@@H]2O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]2O)c(=O)n1 2D coordinates Mol file for the small molecule Search links Involved in 193 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:82903 | RHEA:82904 | RHEA:82905 | RHEA:82906 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
Specific form(s) of this reaction
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RHEA:82983
an N4-{α-Neu5Ac-(2→6)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→2)-α-D-Man-(1→3)-[β-D-Gal-(1→4)-6-O-sulfo-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→2)-α-D-Man-(1→6)]-β-D-Man-(1→4)-β-D-GlcNAc-(1→4)-β-D-GlcNAc}-L-asparaginyl-[protein] + CMP-N-acetyl-β-neuraminate = an N4-{α-Neu5Ac-(2→6)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→2)-α-D-Man-(1→3)-[α-Neu5Ac-(2→6)-β-D-Gal-(1→4)-6-O-sulfo-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-GlcNAc-(1→2)-α-D-Man-(1→6)]-β-D-Man-(1→4)-β-D-GlcNAc-(1→4)-β-D-GlcNAc}-L-asparaginyl-[protein] + CMP + H+
More general form(s) of this reaction
Publications
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Exploiting Substrate Specificities of 6-<i>O</i>-Sulfotransferases to Enzymatically Synthesize Keratan Sulfate Oligosaccharides.
Wu Y., Vos G.M., Huang C., Chapla D., Kimpel A.L.M., Moremen K.W., de Vries R.P., Boons G.J.
Keratan sulfate (KS) is a glycosaminoglycan that is widely expressed in the extracellular matrix of various tissue types, where it is involved in many biological processes. Herein, we describe a chemo-enzymatic approach to preparing well-defined KS oligosaccharides by exploiting the known and newl ... >> More
Keratan sulfate (KS) is a glycosaminoglycan that is widely expressed in the extracellular matrix of various tissue types, where it is involved in many biological processes. Herein, we describe a chemo-enzymatic approach to preparing well-defined KS oligosaccharides by exploiting the known and newly discovered substrate specificities of relevant sulfotransferases. The premise of the approach is that recombinant GlcNAc-6-<i>O</i>-sulfotransferases (CHST2) only sulfate terminal GlcNAc moieties to give GlcNAc6S that can be galactosylated by B4GalT4. Furthermore, CHST1 can modify the internal galactosides of a poly-LacNAc chain; however, it was found that a GlcNAc6S residue greatly increases the reactivity of CHST1 of a neighboring and internal galactoside. The presence of a 2,3-linked sialoside further modulates the site of modification by CHST1, and a galactoside flanked by 2,3-Neu5Ac and GlcNAc6S is preferentially sulfated over the other Gal residues. The substrate specificities of CHST1 and 2 were exploited to prepare a panel of KS oligosaccharides, including selectively sulfated <i>N</i>-glycans. The compounds and several other reference derivatives were used to construct a microarray that was probed for binding by several plant lectins, Siglec proteins, and hemagglutinins of influenza viruses. It was found that not only the sulfation pattern but also the presentation of epitopes as part of an <i>O</i>- or <i>N</i>-glycan determines binding properties. << Less
JACS Au 3:3155-3164(2023) [PubMed] [EuropePMC]
This publication is cited by 16 other entries.