Rhea - reaction knowledgebase

Enzymes

Enzyme class ^help_outline	EC 2.3.1.90 beta-glucogallin O-galloyltransferase
GO Molecular Function ^help_outline	GO:0047201 beta-glucogallin O-galloyltransferase activity

Reaction participants Show >> << Hide

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 1,6-bis-O-galloyl-β-D-glucose Identifier CHEBI:15723 Charge 0 Formula C20H20O14 InChIKey^help_outline LYGRISUQIZNHGM-IVABAYMNSA-N SMILES^help_outline O[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]1COC(=O)c1cc(O)c(O)c(O)c1)OC(=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 D-glucose Identifier CHEBI:4167 (Beilstein: 1281604; 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 152 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:11416	RHEA:11417	RHEA:11418	RHEA:11419
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline
EC numbers ^help_outline	2.3.1.90
Gene Ontology ^help_outline	GO:0047201
KEGG ^help_outline				R00049
MetaCyc ^help_outline		2.3.1.90-RXN

Publications

Biosynthesis of gallotannins. Enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose.

Denzel K., Schilling G., Gross G.G.

Cell-free extracts from Rhus typhina L. (staghorn sumach) leaves were found to catalyze the transfer of the galloyl moiety of β-glucogallin (1-O-galloyl-β-D-glucose) to 1,6-di-O-galloyl-β-D-glucose, resulting in the specific formation of 1,2,6-tri-O-galloyl-β-D-glucose, an intermediate of gallotan ... >> More

Cell-free extracts from Rhus typhina L. (staghorn sumach) leaves were found to catalyze the transfer of the galloyl moiety of β-glucogallin (1-O-galloyl-β-D-glucose) to 1,6-di-O-galloyl-β-D-glucose, resulting in the specific formation of 1,2,6-tri-O-galloyl-β-D-glucose, an intermediate of gallotannin biosynthesis. The reaction product was unequivocally identified by co-chromatography with authentic references using reversed-phase high-performance liquid chromatography and by (1)H-nuclear-magnetic-resonance spectroscopy. << Less

Planta 176:135-137(1988) [PubMed] [EuropePMC]

Comments

Published in: Gross, G.G. Synthesis of mono-galloyl-beta-D-glucose di-galloyl-beta-D-glucose and trigalloyl-beta-D-glucose by beta-glucogallin-dependent galloyltransferases from oak leaves. Z. Natursforsch. C: Biosci. 38 (1983) 519–523.