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- Name help_outline an anthocyanidin 3-O-β-D-glucoside Identifier CHEBI:16307 Charge 1 Formula C21H19O10R2 SMILEShelp_outline OC[C@H]1O[C@@H](Oc2cc3c(O)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 7 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 InChIKeyhelp_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILEShelp_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 231 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an anthocyanidin 3-O-sophoroside Identifier CHEBI:77946 Charge 0 Formula C27H28O15R2 SMILEShelp_outline OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc2cc3c([O-])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 1 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 InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,431 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 InChIKeyhelp_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILEShelp_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 576 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:35419 | RHEA:35420 | RHEA:35421 | RHEA:35422 | |
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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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Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase, due to 4-bp insertions in the gene.
Morita Y., Hoshino A., Kikuchi Y., Okuhara H., Ono E., Tanaka Y., Fukui Y., Saito N., Nitasaka E., Noguchi H., Iida S.
Bright blue or red flowers in the Japanese morning glory (Ipomoea nil) contain anthocyanidin 3-O-sophoroside derivatives, whereas the reddish-brown or purplish-gray petals in its dusky mutants accumulate anthocyanidin 3-O-glucoside derivatives. The Dusky gene was found to encode a novel glucosyltr ... >> More
Bright blue or red flowers in the Japanese morning glory (Ipomoea nil) contain anthocyanidin 3-O-sophoroside derivatives, whereas the reddish-brown or purplish-gray petals in its dusky mutants accumulate anthocyanidin 3-O-glucoside derivatives. The Dusky gene was found to encode a novel glucosyltransferase, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase (3GGT), which mediates the glucosylation of anthocyanidin 3-O-glucosides to yield anthocyanidin 3-O-sophorosides. Ipomoea nil carries one copy of the 3GGT gene that contains no intron and produces 1.6-kbp transcripts mainly in the petals and tubes of flower buds at around 24 h before flower opening. The gene products of both In3GGT in I. nil and Ip3GGT in the common morning glory (Ipomoea purpurea) comprise 459 amino acids and showed a close relationship to the petunia UDP-rhamnose:anthocyanidin 3-O-glucoside-6''-O-rhamnosyltransferase (3RT), which controls the addition of a rhamnose molecule to anthocyanidin 3-O-glucosides for conversion into anthocyanidin 3-O-rutinosides. All of the 30 dusky mutants tested were found to carry the 4-bp insertion mutations GGAT or CGAT at an identical position near the 3' end of the gene, and the insertions caused frameshift mutations. The expected 3GGT enzymatic activities were found in the crude extracts of Escherichia coli, in which the 3GGT cDNA of I. nil or I. purpurea was expressed, while no such activity was detected in the extracts expressed with the dusky mutant cDNAs containing 4-bp insertions. Moreover, the introduced Ip3GGT cDNA efficiently produced 3GGT that converted cyanidin 3-O-glucoside into cyanidin 3-O-sophoroside in transgenic petunia plants. << Less