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MetaCyc Enzyme: UDP-D-glucose:delphinidin-3-O-β-D-glucoside 5-O-glucosyltransferase [multifunctional]

Gene: PF3R4 Accession Number: G-9307 (MetaCyc)

Species: Perilla frutescens

Molecular Weight of Polypeptide: 50.973 kD (from nucleotide sequence)

Unification Links: Entrez:BAA36421

Relationship Links: Entrez-Nucleotide:PART-OF:AB013596

Gene-Reaction Schematic: ?

Gene-Reaction Schematic


Enzymatic reaction of: UDP-D-glucose:delphinidin-3-O-β-D-glucoside 5-O-glucosyltransferase

UDP-α-D-glucose + delphinidin-3-O-β-D-glucoside <=> delphinidin 3,5-di-O-β-D-glucoside + UDP + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: superpathway of anthocyanin biosynthesis (from delphinidin 3-O-glucoside) , gentiodelphin biosynthesis

Summary:
The cDNA encoding for the anthocyanin 5-O-glucosyltransferase (5-GT) in Perilla frutescens was isolated and recombinant expressed in yeast. The molecular function was shown to express anthocyanin 5-O-glucosyltransferase activity converting anthocyanidin 3-O-glucoside to anthocyanidin 3,5-diglucoside. The best in vitro substrate was cyanidine 3-O-glucoside followed by delphinidin 3-O-glucoside and pelargonidin 3-O-glucoside. Some activity was also observed towards anthocyanidin-3-O-acylglucoside. The investigation of red and green forms of Perilla frutescens revealed that the 5-GT gene was specifically expressed in the leaves of the red form, but not in those of the green form. The expression of the 5-GT gene was induced by illumination with white light. [Yamazaki99].

Inhibitors (Unknown Mechanism): p-chloromercuribenzoate [Yamazaki99]

pH(opt): 8.0-8.5 [Yamazaki99]


Enzymatic reaction of: UDP-D-glucose:cyanidin 3-(p-coumaroyl)-glucoside 5-O-glucosyltransferase

EC Number: 2.4.1.-

UDP-α-D-glucose + cyanidin 3-(p-coumaroyl)-glucoside <=> shisonin + UDP + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: shisonin biosynthesis , superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside)

Summary:
The cDNA encoding for the anthocyanin 5-O-glucosyltransferase (5-GT) in Perilla frutescens was isolated and recombinant expressed in yeast. The molecular function was shown to express anthocyanin 5-O-glucosyltransferase activity converting anthocyanidin 3-O-glucoside to anthocyanidin 3,5-diglucoside. The best in vitro substrate was cyanidine 3-O-glucoside followed by delphinidin 3-O-glucoside and pelargonidin 3-O-glucoside. Some activity was also observed towards anthocyanidin-3-O-acylglucoside. The investigation of red and green forms of Perilla frutescens revealed that the 5-GT gene was specifically expressed in the leaves of the red form, but not in those of the green form. The expression of the 5-GT gene was induced by illumination with white light. [Yamazaki99].

Inhibitors (Unknown Mechanism): p-chloromercuribenzoate [Yamazaki99]


Enzymatic reaction of: UDP-D-glucose:cyanidin-3-O-β-D-glucoside 5-O-glucosyltransferase

cyanidin-3-O-β-D-glucoside + UDP-α-D-glucose <=> cyanidin 3,5-di-O-β-D-glucoside + UDP + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: shisonin biosynthesis , superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside)

Summary:
The cDNA encoding for the anthocyanin 5-O-glucosyltransferase (5-GT) in Perilla frutescens was isolated and recombinant expressed in yeast. The molecular function was shown to express anthocyanin 5-O-glucosyltransferase activity converting anthocyanidin 3-O-glucoside to anthocyanidin 3,5-diglucoside. The best in vitro substrate was cyanidine 3-O-glucoside followed by delphinidin 3-O-glucoside and pelargonidin 3-O-glucoside. Some activity was also observed towards anthocyanidin-3-O-acylglucoside. The investigation of red and green forms of Perilla frutescens revealed that the 5-GT gene was specifically expressed in the leaves of the red form, but not in those of the green form. The expression of the 5-GT gene was induced by illumination with white light. [Yamazaki99].

Inhibitors (Unknown Mechanism): p-chloromercuribenzoate [Yamazaki99]

Kinetic Parameters:

Substrate
Km (μM)
Citations
cyanidin-3-O-β-D-glucoside
31.4
[Yamazaki99]
UDP-α-D-glucose
940.0
[Yamazaki99]

pH(opt): 8.0-8.5 [Yamazaki99]


Enzymatic reaction of: UDP-D-glucose:pelargonidin-3-O-β-D-glucoside 5-O-glucosyltransferase

EC Number: 2.4.1.-

pelargonidin-3-O-β-D-glucoside + UDP-α-D-glucose <=> pelargonidin-3,5-di-O-β-D-glucoside + UDP + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: superpathway of anthocyanin biosynthesis (from pelargonidin 3-O-glucoside) , pelargonidin conjugates biosynthesis , salvianin biosynthesis

Summary:
The cDNA encoding for the anthocyanin 5-O-glucosyltransferase (5-GT) in Perilla frutescens was isolated and recombinant expressed in yeast. The molecular function was shown to express anthocyanin 5-O-glucosyltransferase activity converting anthocyanidin 3-O-glucoside to anthocyanidin 3,5-diglucoside. The best in vitro substrate was cyanidine 3-O-glucoside followed by delphinidin 3-O-glucoside and pelargonidin 3-O-glucoside. Some activity was also observed towards anthocyanidin-3-O-acylglucoside. The investigation of red and green forms of Perilla frutescens revealed that the 5-GT gene was specifically expressed in the leaves of the red form, but not in those of the green form. The expression of the 5-GT gene was induced by illumination with white light. [Yamazaki99].

Inhibitors (Unknown Mechanism): p-chloromercuribenzoate [Yamazaki99]

pH(opt): 8.0-8.5 [Yamazaki99]


References

Yamazaki99: Yamazaki M, Gong Z, Fukuchi-Mizutani M, Fukui Y, Tanaka Y, Kusumi T, Saito K (1999). "Molecular cloning and biochemical characterization of a novel anthocyanin 5-O-glucosyltransferase by mRNA differential display for plant forms regarding anthocyanin." J Biol Chem 274(11);7405-11. PMID: 10066805


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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