Rhea - reaction knowledgebase

Enzymes

Enzyme class ^help_outline	EC 2.3.1.143 beta-glucogallin--tetrakisgalloylglucose O-galloyltransferase
GO Molecular Function ^help_outline	GO:0047176 beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase activity

Reaction participants Show >> << Hide

Name ^help_outline 1,2,3,6-tetrakis-O-galloyl-β-D-glucose Identifier CHEBI:17527 (Beilstein: 3584855; CAS: 79886-50-3) ^help_outline Charge 0 Formula C34H28O22 InChIKey^help_outline RATQVALKDAUZBW-XPMKZLBQSA-N SMILES^help_outline O[C@@H]1[C@@H](COC(=O)c2cc(O)c(O)c(O)c2)O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H]1OC(=O)c1cc(O)c(O)c(O)c1 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 1-O-galloyl-β-D-glucose Identifier CHEBI:15834 (CAS: 554-37-0) ^help_outline Charge 0 Formula C13H16O10 InChIKey^help_outline GDVRUDXLQBVIKP-HQHREHCSSA-N SMILES^help_outline OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](O)[C@@H](O)[C@@H]1O 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 1,2,3,4,6-pentakis-O-galloyl-β-D-glucose Identifier CHEBI:145902 Charge -1 Formula C41H31O26 InChIKey^help_outline QJYNZEYHSMRWBK-NIKIMHBISA-M SMILES^help_outline [C@@H]1(COC(=O)C=2C=C(C(=C(C2)O)O)O)[C@@H](OC(C=3C=C(C(=C(C3)O)O)O)=O)[C@H](OC(C=4C=C(C(=C(C4)O)O)O)=O)[C@H]([C@@H](O1)OC(=O)C5=CC(=C(C(=C5)O)[O-])O)OC(=O)C=6C=C(C(=C(C6)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
Name ^help_outline D-glucose Identifier CHEBI:4167 (CAS: 2280-44-6) ^help_outline Charge 0 Formula C6H12O6 InChIKey^help_outline WQZGKKKJIJFFOK-GASJEMHNSA-N SMILES^help_outline OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 163 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 InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_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:19109	RHEA:19110	RHEA:19111	RHEA:19112
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline
EC numbers ^help_outline	2.3.1.143
Gene Ontology ^help_outline	GO:0047176
KEGG ^help_outline				R04498
MetaCyc ^help_outline		2.3.1.143-RXN

Publications

Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose.

Cammann J., Denzel K., Schilling G., Gross G.G.

An acyltransferase was detected in young leaves of pedunculate oak (Quercus robur) that catalyzed the formation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose, the common precursor of gallotannins and the related ellagitannins. This enzyme depended on beta-glucogallin (1-O-galloyl-beta-D-glucose) as ... >> More

An acyltransferase was detected in young leaves of pedunculate oak (Quercus robur) that catalyzed the formation of 1,2,3,4,6-penta-O-galloyl-beta-D-glucose, the common precursor of gallotannins and the related ellagitannins. This enzyme depended on beta-glucogallin (1-O-galloyl-beta-D-glucose) as acyl donor; 1,2,3,6-tetra-O-galloyl-beta-D-glucose was specifically required as acceptor molecule, whereas no reaction occurred with the 1,2,4,6-isomer of this substrate. The partially purified enzyme (Mr 260,000) was stable between pH 5.0 and 6.5; highest activities were observed at pH 6.3 and 40 degrees C. Km values of 2.3 and 1.0 mM, respectively, were determined for the substrates beta-glucogallin and tetragalloylglucose. In accordance with stoichiometric studies, the systematic name "beta-glucogallin: 1,2,3,6-tetra-O-galloylglucose 4-O-galloyltransferase" is proposed for this new enzyme. << Less

Arch Biochem Biophys 273:58-63(1989) [PubMed] [EuropePMC]

RHEA:19109 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose + 1-O-galloyl-beta-D-glucose = 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose + D-glucose + H(+)

Enzymes

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Cross-references

Publications

Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose.