Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme class ^help_outline	EC 2.4.1.238 delphinidin 3,5-di-O-glucoside 3'-O-glucosyltransferase
GO Molecular Function ^help_outline	GO:0033837 anthocyanin 3'-O-beta-glucosyltransferase activity

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Name ^help_outline delphinidin 3,5-bis-O-β-D-glucoside Identifier CHEBI:77838 Charge 0 Formula C27H30O17 InChIKey^help_outline XCTGXGVGJYACEI-LCENJUANSA-N SMILES^help_outline OC[C@H]1O[C@@H](Oc2cc3c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc([O-])cc3[o+]c2-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 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) ^help_outline Charge -2 Formula C15H22N2O17P2 InChIKey^help_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILES^help_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 258 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline delphinidin 3,3',5-tri-O-β-D-glucoside Identifier CHEBI:77844 Charge 0 Formula C33H40O22 InChIKey^help_outline YDAVXGXZAIUFTB-KCRRSQHJSA-N SMILES^help_outline OC[C@H]1O[C@@H](Oc2cc(cc(O)c2O)-c2[o+]c3cc([O-])cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3cc2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O 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 UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKey^help_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILES^help_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 637 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:35627	RHEA:35628	RHEA:35629	RHEA:35630
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins
EC numbers ^help_outline	2.4.1.238
Gene Ontology ^help_outline	GO:0033837
KEGG ^help_outline				R07266
MetaCyc ^help_outline		RXN-8231

Publications

Biochemical and molecular characterization of a novel UDP-glucose:anthocyanin 3'-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian.

Fukuchi-Mizutani M., Okuhara H., Fukui Y., Nakao M., Katsumoto Y., Yonekura-Sakakibara K., Kusumi T., Hase T., Tanaka Y.

Gentian (Gentiana triflora) blue petals predominantly contain an unusually blue and stable anthocyanin, delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3'-O-(6-O-caffeoyl-glucoside) (gentiodelphin). Glucosylation and the subsequent acylation of the 3'-hydroxy group of the B-ring of anthocyani ... >> More

Gentian (Gentiana triflora) blue petals predominantly contain an unusually blue and stable anthocyanin, delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3'-O-(6-O-caffeoyl-glucoside) (gentiodelphin). Glucosylation and the subsequent acylation of the 3'-hydroxy group of the B-ring of anthocyanins are important to the stabilization of and the imparting of bluer color to these anthocyanins. The enzymes and their genes involved in these modifications of the B-ring, however, have not been characterized, purified, or isolated to date. In this study, we purified a UDP-glucose (Glc):anthocyanin 3'-O-glucosyltransferase (3'GT) enzyme to homogeneity from gentian blue petals and isolated a cDNA encoding a 3'GT based on the internal amino acid sequences of the purified 3'GT. The deduced amino acid sequence indicates that 3'GT belongs to the same subfamily as a flavonoid 7-O-glucosyltransferase from Schutellaria baicalensis in the plant glucosyltransferase superfamily. Characterization of the enzymatic properties using the recombinant 3'GT protein revealed that, in contrast to most of flavonoid glucosyltransferases, it has strict substrate specificity: 3'GT specifically glucosylates the 3'-hydroxy group of delphinidin-type anthocyanins containing Glc groups at 3 and 5 positions. The enzyme specifically uses UDP-Glc as the sugar donor. The specificity was confirmed by expression of the 3'GT cDNA in transgenic petunia (Petunia hybrida). This is the first report of the gene isolation of a B-ring-specific glucosyltransferase of anthocyanins, which paves the way to modification of flower color by production of blue anthocyanins. << Less

Plant Physiol. 132:1652-1663(2003) [PubMed] [EuropePMC]

RHEA:35627 delphinidin 3,5-bis-O-beta-D-glucoside + UDP-alpha-D-glucose = delphinidin 3,3',5-tri-O-beta-D-glucoside + UDP + H(+)

Enzymes

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Cross-references

Publications

Biochemical and molecular characterization of a novel UDP-glucose:anthocyanin 3'-O-glucosyltransferase, a key enzyme for blue anthocyanin biosynthesis, from gentian.