Reaction participants Show >> << Hide
- Name help_outline (E)-4-coumaroyl-CoA Identifier CHEBI:85008 Charge -4 Formula C30H38N7O18P3S InChIKeyhelp_outline DMZOKBALNZWDKI-MATMFAIHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)\C=C\c1ccc(O)cc1 2D coordinates Mol file for the small molecule Search links Involved in 16 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an anthocyanidin 3,5-di-O-β-D-glucoside Identifier CHEBI:57503 Charge 0 Formula C27H28O15R2 SMILEShelp_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([*])c(O)c([*])c2)[C@H](O)[C@@H](O)[C@@H]1O 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 an anthocyanidin 3-O-β-D-glucoside 5-O-β-D-[(6-O-(E)-4-coumaroyl)glucoside] Identifier CHEBI:144773 Charge 0 Formula C36H34O17R2 SMILEShelp_outline C1(=C(C=C2C(OC3O[C@@H]([C@@H](O)[C@@H]([C@H]3O)O)COC(/C=C/C4=CC=C(C=C4)O)=O)=CC(=CC2=[O+]1)[O-])O[C@@H]5O[C@@H]([C@@H](O)[C@@H]([C@H]5O)O)CO)C6=CC(=C(O)C(=C6)*)* 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 CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,468 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:15661 | RHEA:15662 | RHEA:15663 | RHEA:15664 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Anthocyanin 5-aromatic acyltransferase from Gentiana triflora. Purification, characterization and its role in anthocyanin biosynthesis.
Fujiwara H., Tanaka Y., Fukui Y., Nakao M., Ashikari T., Kusumi T.
Acylation with hydroxycinnamic acids stabilizes anthocyanins and makes their colour bluer (bathochromic shift). We purified to homogeneity one acylation enzyme, hydroxycinnamoyl-CoA:anthocyanidin 3,5-diglucoside 5-O-glucoside-6"'-O-hydroxycinnamoyltransferase, from blue petals of Gentiana triflora ... >> More
Acylation with hydroxycinnamic acids stabilizes anthocyanins and makes their colour bluer (bathochromic shift). We purified to homogeneity one acylation enzyme, hydroxycinnamoyl-CoA:anthocyanidin 3,5-diglucoside 5-O-glucoside-6"'-O-hydroxycinnamoyltransferase, from blue petals of Gentiana triflora. It is a single polypeptide protein of 52 kDa with a pI of 4.6. It catalyzes the transfer of the p-coumaric acid and caffeic acid from their CoA esters to the 5-glucosyl moiety of anthocyanidin 3,5-diglucosides but could not use malonyl-CoA as an acyl donor. Neither anthocyanidin 3-monoglucoside nor anthocyanins aromatically acylated at the 3-glucosyl moiety could be acylated by this enzyme. Aromatic acylation of anthocyanidin 3,5-diglucoside by this enzyme caused a bathochromic shift and increased pigment stability in neutral to weakly basic pH. Other anthocyanins from the petals of G. triflora were isolated and their structures were determined by fast-atom-bombardment MS and NMR. The biosynthetic pathway of gentiodelphin, a diacylated anthocyanin accumulating in G. triflora petals, is proposed on the basis of these results. << Less
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cDNA cloning, gene expression and subcellular localization of anthocyanin 5-aromatic acyltransferase from Gentiana triflora.
Fujiwara H., Tanaka Y., Yonekura-Sakakibara K., Fukuchi-Mizutani M., Nakao M., Fukui Y., Yamaguchi M., Ashikari T., Kusumi T.
Acylation of anthocyanins with hydroxycinnamic acid derivatives is one of the most important and less under-stood modification reactions during anthocyanin biosynthesis. Anthocyanin aromatic acyltransferase catalyses the transfer of hydroxycinnamic acid moieties from their CoA esters to the glycos ... >> More
Acylation of anthocyanins with hydroxycinnamic acid derivatives is one of the most important and less under-stood modification reactions during anthocyanin biosynthesis. Anthocyanin aromatic acyltransferase catalyses the transfer of hydroxycinnamic acid moieties from their CoA esters to the glycosyl groups of anthocyanins. A full-length cDNA encoding the anthocyanin 5-aromatic acyltransferase (5AT) (EC 2.3.1.153) that acylates the glucose bound at the 5-position of anthocyanidin 3,5-diglucoside was isolated from petals of Gentiana triflora on the basis of the amino acid sequence of the purified enzyme. The isolated full-length cDNA had an open reading frame of 469 amino acids and the calculated molecular weight was 52,736. The deduced amino acid sequence contains consensus motifs that are conserved among the putative acyl CoA-mediated acyltransferases, and this indicates that 5AT is a member of a proposed superfamily of multi-functional acyltransferases (St-Pierre et al. (1998) Plant J. 14, 703-713). The cDNA was expressed in Escherichia coli and yeast, and confirmed to encode 5AT. The enzymatic characteristics of the recombinant 5AT were consistent with those of the native gentian 5AT. Immunoblot analysis using specific antibodies to 5AT showed that the 5AT protein is present in petals, but not in sepals, stems or leaves of G. triflora. RNA blot analysis showed that the 5AT gene is expressed only in petals and that its expression is temporally regulated during flower development coordinately with other anthocyanin biosynthetic genes. Immunohistochemical analysis demonstrated that the 5AT protein is specifically expressed in the outer epidermal cells of gentian petals and that it is localized mainly in the cytosol. << Less