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Namehelp_outline
3-O-{β-D-galactosyl-(1→3)-[N-acetyl-β-D-glucosaminyl-(1→6)]-N-acetyl-α-D-galactosaminyl}-L-seryl-[protein]
Identifier
RHEA-COMP:14419
Reactive part
help_outline
- Name help_outline O3-{β-D-galactosyl-(1→3)-[N-acetyl-β-D-glucosaminyl-(1→6)]-N-acetyl-α-D-galactosaminyl}-L-serine residue Identifier CHEBI:139605 Charge 0 Formula C25H41N3O17 SMILEShelp_outline [C@@H]1([C@H](O[C@@H]([C@@H]([C@@H]1O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)CO[C@]3([C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(C)=O)[H])OC[C@@H](C(*)=O)N*)NC(=O)C 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 UDP-N-acetyl-α-D-glucosamine Identifier CHEBI:57705 (Beilstein: 4286654) help_outline Charge -2 Formula C17H25N3O17P2 InChIKeyhelp_outline LFTYTUAZOPRMMI-CFRASDGPSA-L SMILEShelp_outline CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 88 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
3-O-{β-D-GlcNAc-(1→3)-β-D-Gal-(1→3)-[β-D-GlcNAc-(1→6)]-α-D-GalNAc}-L-seryl-[protein]
Identifier
RHEA-COMP:14421
Reactive part
help_outline
- Name help_outline O3-{β-D-GlcNAc-(1→3)-β-D-Gal-(1→3)-[β-D-GlcNAc-(1→6)]-α-D-GalNAc}-L-serine residue Identifier CHEBI:139611 Charge 0 Formula C33H54N4O22 SMILEShelp_outline [C@@H]1([C@H](O[C@@H]([C@@H]([C@@H]1O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(C)=O)O)O)O)CO[C@]4([C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)NC(C)=O)[H])OC[C@@H](C(*)=O)N*)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 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 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 542 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:56220 | RHEA:56221 | RHEA:56222 | RHEA:56223 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Identification and characterization of three novel beta 1,3-N-acetylglucosaminyltransferases structurally related to the beta 1,3-galactosyltransferase family.
Shiraishi N., Natsume A., Togayachi A., Endo T., Akashima T., Yamada Y., Imai N., Nakagawa S., Koizumi S., Sekine S., Narimatsu H., Sasaki K.
We have isolated three types of cDNAs encoding novel beta1,3-N-acetylglucosaminyltransferases (designated beta3Gn-T2, -T3, and -T4) from human gastric mucosa and the neuroblastoma cell line SK-N-MC. These enzymes are predicted to be type 2 transmembrane proteins of 397, 372, and 378 amino acids, r ... >> More
We have isolated three types of cDNAs encoding novel beta1,3-N-acetylglucosaminyltransferases (designated beta3Gn-T2, -T3, and -T4) from human gastric mucosa and the neuroblastoma cell line SK-N-MC. These enzymes are predicted to be type 2 transmembrane proteins of 397, 372, and 378 amino acids, respectively. They share motifs conserved among members of the beta1,3-galactosyltransferase family and a beta1,3-N-acetylglucosaminyltransferase (designated beta3Gn-T1), but show no structural similarity to another type of beta1,3-N-acetylglucosaminyltransferase (iGnT). Each of the enzymes expressed by insect cells as a secreted protein fused to the FLAG peptide showed beta1,3-N-acetylglucosaminyltransferase activity for type 2 oligosaccharides but not beta1,3-galactosyltransferase activity. These enzymes exhibited different substrate specificity. Transfection of Namalwa KJM-1 cells with beta3Gn-T2, -T3, or -T4 cDNA led to an increase in poly-N-acetyllactosamines recognized by an anti-i-antigen antibody or specific lectins. The expression profiles of these beta3Gn-Ts were different among 35 human tissues. beta3Gn-T2 was ubiquitously expressed, whereas expression of beta3Gn-T3 and -T4 was relatively restricted. beta3Gn-T3 was expressed in colon, jejunum, stomach, esophagus, placenta, and trachea. beta3Gn-T4 was mainly expressed in brain. These results have revealed that several beta1,3-N-acetylglucosaminyltransferases form a family with structural similarity to the beta1,3-galactosyltransferase family. Considering the differences in substrate specificity and distribution, each beta1,3-N-acetylglucosaminyltransferase may play different roles. << Less
J. Biol. Chem. 276:3498-3507(2001) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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The separation by liquid chromatography (under elevated pressure) of phenyl, benzyl, and O-nitrophenyl glycosides of oligosaccharides. Analysis of substrates and products for four N-acetyl-D-glucosaminyl-transferases involved in mucin synthesis.
Brockhausen I., Rachaman E.S., Matta K.L., Schachter H.
Liquid chromatography under elevated pressure (h.p.l.c.) has been applied to the separation of the phenyl, benzyl, and O-nitrophenyl glycosides of 2-acetamido-2-deoxy-D-galactopyranose and of various mucin-type, di-, tri-, and tetra-saccharides. The separations were carried out with a Whatman Part ... >> More
Liquid chromatography under elevated pressure (h.p.l.c.) has been applied to the separation of the phenyl, benzyl, and O-nitrophenyl glycosides of 2-acetamido-2-deoxy-D-galactopyranose and of various mucin-type, di-, tri-, and tetra-saccharides. The separations were carried out with a Whatman Partisil PXS 5/25 PAC column and various proportions of acetonitrile and water in the mobile phase. These methods were subsequently used to separate the substrates and products of the following N-acetylglucosaminyltransferase reactions: UDP-GlcNAc + beta-Gal-(1 leads to 3)-GalNAc-R leads to beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R + UDP (1); UDP-GlcNAc + beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R leads to beta-GlcNAc-(1 leads to 3)-beta-Gal-(1 leads to 3)-[beta-GlcNAc-(1 leads to 6)]-GalNAc-R + UDP (2); UDP-GlcNAc + GalNAc-R' leads to beta-GlcNAc-(1 leads to 3)-GalNAc-R' + UDP (3); and UDP-GlcNAc + beta-GlcNAc-(1 leads to 3)-GalNAc-R' leads to beta-GlcNAc-(1 leads to 6)-[beta-GlcNAc-(1 leads to 3)]-GalNAc-R' + UDP (4), where R is = benzyl or o-nitrophenyl, and R' = benzyl or phenyl alpha-D-glycoside. Reaction 1 is catalyzed by a transferase in canine submaxillary glands and porcine gastric mucosa, and reaction 2 by an enzyme in porcine gastric mucosa. Enzyme activities catalyzing reactions 3 and 4 have recently been demonstrated in rat colonic mucosa. Liquid chromatography can be used at the preparative level for the purification and identification of the transferase products, and at the analytical level in the assay of glycosyltransferases. << Less
Carbohydr Res 120:3-16(1983) [PubMed] [EuropePMC]
This publication is cited by 8 other entries.
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Novel sulfated lymphocyte homing receptors and their control by a Core1 extension beta 1,3-N-acetylglucosaminyltransferase.
Yeh J.-C., Hiraoka N., Petryniak B., Nakayama J., Ellies L.G., Rabuka D., Hindsgaul O., Marth J.D., Lowe J.B., Fukuda M.
L-selectin mediates lymphocyte homing by facilitating lymphocyte adhesion to addressins expressed in the high endothelial venules (HEV) of secondary lymphoid organs. Peripheral node addressin recognized by the MECA-79 antibody is apparently part of the L-selectin ligand, but its chemical nature ha ... >> More
L-selectin mediates lymphocyte homing by facilitating lymphocyte adhesion to addressins expressed in the high endothelial venules (HEV) of secondary lymphoid organs. Peripheral node addressin recognized by the MECA-79 antibody is apparently part of the L-selectin ligand, but its chemical nature has been undefined. We now identify a sulfated extended core1 mucin-type O-glycan, Gal beta 1-->4(sulfo-->6)GlcNAc beta 1-->3Gal beta 1-->3GalNAc, as the MECA-79 epitope. Molecular cloning of a HEV-expressed core1-beta 1,3-N-acetylglucosaminyltransferase (Core1-beta 3GlcNAcT) enabled the construction of the 6-sulfo sialyl Lewis x on extended core1 O-glycans, recapitulating the potent L-selectin-mediated, shear-dependent adhesion observed with novel L-selectin ligands derived from core2 beta1,6-N-acetylglucosaminyltransferase-I null mice. These results identify Core1-beta 3GlcNAcT and its cognate extended core1 O-glycans as essential participants in the expression of the MECA-79-positive, HEV-specific L-selectin ligands required for lymphocyte homing. << Less
Cell 105:957-969(2001) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.