Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	3 proteins
Enzyme class ^help_outline	EC 3.1.4.45 N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase
GO Molecular Function ^help_outline	GO:0003944 N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase activity

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Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline N⁴-[6-(N-acetyl-α-D-glucosaminyl-1-phospho)-α-D-mannosyl-(1→2)-α-D-mannosyl-(glycan)]-L-asparaginyl-[protein] Identifier RHEA-COMP:14508 Reactive part ^help_outline
- Name ^help_outline N⁴-[6-(N-acetyl-α-D-glucosaminyl-1-phospho)-α-D-mannosyl-(1→2)-α-D-mannosyl-glycan]-L-asparagine residue Identifier CHEBI:140369 Charge -1 Formula C24H39N3O21PR SMILES^help_outline [C@H]1([C@H](O[C@@H]([C@H]([C@@H]1O)O)CO)O*NC(C[C@@H](C(*)=O)N*)=O)O[C@@H]2[C@@H]([C@H]([C@H]([C@H](O2)COP(O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(C)=O)([O-])=O)O)O)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 2 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_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 N⁴-[6-phospho-α-D-mannosyl-(1→2)-α-D-mannosyl-(glycan)]-L-asparaginyl-[protein] Identifier RHEA-COMP:14509 Reactive part ^help_outline
- Name ^help_outline N⁴-[6-phospho-α-D-mannosyl-(1→2)-α-D-mannosyl-glycan]-L-asparagine residue Identifier CHEBI:140371 Charge -2 Formula C16H25N2O16PR SMILES^help_outline [C@H]1([C@H](O[C@@H]([C@H]([C@@H]1O)O)CO)O*NC(C[C@@H](C(*)=O)N*)=O)O[C@@H]2[C@@H]([C@H]([C@H]([C@H](O2)COP([O-])([O-])=O)O)O)O 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
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline N-acetyl-D-glucosamine Identifier CHEBI:506227 (Beilstein: 1913592; CAS: 7512-17-6) ^help_outline Charge 0 Formula C8H15NO6 InChIKey^help_outline OVRNDRQMDRJTHS-RTRLPJTCSA-N SMILES^help_outline CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 23 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:24372	RHEA:24373	RHEA:24374	RHEA:24375
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	3 proteins
EC numbers ^help_outline	3.1.4.45
Gene Ontology ^help_outline	GO:0003944
KEGG ^help_outline				R04373

Publications

Processing of the phosphorylated recognition marker in lysosomal enzymes. Characterization and partial purification of a microsomal alpha-N-acetylglucosaminyl phosphodiesterase.

Waheed A., Hasilik A., von Figura K.

N-Acetylglucosamine(1)phospho(6)mannose groups recently identified in lysosomal enzymes were proposed to be precursors of the recognition markers terminating with mannose 6-phosphate (Tabas, I., and Kornfeld, S. (1980) J. Biol. Chem. 225, 6633-6639; Hasilik, A., Klein, U., Waheed, A., Strecker, G. ... >> More

N-Acetylglucosamine(1)phospho(6)mannose groups recently identified in lysosomal enzymes were proposed to be precursors of the recognition markers terminating with mannose 6-phosphate (Tabas, I., and Kornfeld, S. (1980) J. Biol. Chem. 225, 6633-6639; Hasilik, A., Klein, U., Waheed, A., Strecker, G., and von Figura, K. (1980) Proc. Natl. Acad. Sci. U.S.A. 77, 7074-7078). To study the presumptive enzyme removing N-acetylglucosamine from the diester, an assay was developed using a radioactive oligosaccharide containing diester groups of the above structure. An alpha-N-acetylglucosaminyl phosphodiesterase cleaving this substrate in vitro was found in human placenta and in rat liver. The enzyme was solubilized from the microsomal fraction of human placenta and more than 800-fold purified with 75% yield. It is distinct from the lysosomal alpha-N-acetylglucosaminidase by the criteria of immunological cross-reactivity, substrate specificity, and heat stability. The partially purified enzyme cleaves alpha-N-acetylglucosamine phosphodiester bonds in oligosaccharides from lysosomal enzymes, in lysosomal enzymes, and in UDP-N-acetylglucosamine. We propose that the microsomal alpha-N-acetylglucosaminyl phosphodiesterase is involved in the processing of the phosphorylated recognition marker in lysosomal enzymes. << Less

J Biol Chem 256:5717-5721(1981) [PubMed] [EuropePMC]

RHEA:24372 H2O + N(4)-[6-(N-acetyl-alpha-D-glucosaminyl-1-phospho)-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(glycan)]-L-asparaginyl-[protein] = H(+) + N(4)-[6-phospho-alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(glycan)]-L-asparaginyl-[protein] + N-acetyl-D-glucosamine

Enzymes

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Cross-references

Publications

Processing of the phosphorylated recognition marker in lysosomal enzymes. Characterization and partial purification of a microsomal alpha-N-acetylglucosaminyl phosphodiesterase.