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Namehelp_outline
a 3-O-[β-D-galactosyl-(1→3)-N-acetyl-α-D-galactosaminyl]-L-threonyl-[protein]
Identifier
RHEA-COMP:13923
Reactive part
help_outline
- Name help_outline a 3-O-[β-D-galactosyl-(1→3)-N-acetyl-α-D-galactosaminyl]-L-threonine residue Identifier CHEBI:137950 Charge 0 Formula C18H30N2O12 SMILEShelp_outline [C@H]1([C@@H]([C@H]([C@H]([C@H](O1)CO)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)NC(=O)C)O[C@@H]([C@@H](C(=O)*)N*)C 2D coordinates Mol file for the small molecule Search links Involved in 6 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 91 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
a 3-O-{β-D-galactosyl-(1→3)-[N-acetyl-α-neuraminosyl-(2→6)]-N-acetyl-α-D-galactosaminyl}-L-threonyl-[protein]
Identifier
RHEA-COMP:19722
Reactive part
help_outline
- Name help_outline a 3-O-{β-D-galactosyl-(1→3)-[N-acetyl-α-neuraminosyl-(2→6)]-N-acetyl-α-D-galactosaminyl}-L-threonine residue Identifier CHEBI:231971 Charge -1 Formula C29H46N3O20 SMILEShelp_outline [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@H](O[C@H](C)[C@H](N-*)C(-*)=O)[C@H](NC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O)C([O-])=O)[C@H](O)[C@H](O)CO 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 173 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 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:81651 | RHEA:81652 | RHEA:81653 | RHEA:81654 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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| KEGG help_outline |
Related reactions help_outline
More general form(s) of this reaction
Publications
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Efficient chemoenzymatic synthesis of O-linked sialyl oligosaccharides.
Blixt O., Allin K., Pereira L., Datta A., Paulson J.C.
The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)-antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthe ... >> More
The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)-antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc I) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal I). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(2-6)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(2-6)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans. << Less
J Am Chem Soc 124:5739-5746(2002) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.