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Information on EC 2.4.1.238 - delphinidin 3,5-di-O-glucoside 3'-O-glucosyltransferase

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EC Tree

2 Transferases

2.4 Glycosyltransferases

2.4.1 Hexosyltransferases

2.4.1.238 delphinidin 3,5-di-O-glucoside 3'-O-glucosyltransferase

IUBMB Comments

Isolated from the plant Gentiana triflora (clustered gentian).

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The expected taxonomic range for this enzyme is: Gentiana triflora

Reaction Schemes

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UDP-alpha-D-glucose

delphinidin 3,5-di-O-beta-D-glucoside

UDP

delphinidin 3,3',5-tri-O-beta-D-glucoside

Synonyms

3'GT, anthocyanin 3'-O-beta-D-glucosyltransferase, UDP-glucose:anthocyanin 3'-O-glucosyltransferase, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

3'GT

Gentiana triflora

Q8H0F2

657052

anthocyanin 3'-O-beta-D-glucosyltransferase

UDP-glucose:anthocyanin 3'-O-glucosyltransferase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

UDP-alpha-D-glucose + delphinidin 3,5-di-O-beta-D-glucoside = UDP + delphinidin 3,3',5-tri-O-beta-D-glucoside

2 entries

UDP-alpha-D-glucose + delphinidin 3,5-di-O-beta-D-glucoside = UDP + delphinidin 3,3',5-tri-O-beta-D-glucoside

this enzyme specifically glucosylates the 3'-hydroxy group of delphinidin-3-O-glucosyl-5-O-(6-O-caffeoylglucosyl)-3'-O-(6-O-caffeoylglucoside)-type anthocyanins containing glucose groups at the 3 and 5 positions, acts on delphinidin 3,5-di-O-glucoside in gentian, Gentiana triflora

Gentiana triflora

Q8H0F2

657052

UDP-alpha-D-glucose + delphinidin 3,5-di-O-beta-D-glucoside = UDP + delphinidin 3,3',5-tri-O-beta-D-glucoside

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REACTION TYPE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

transfer of glycosyl group

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PATHWAY SOURCE

PATHWAYS

KEGG

Anthocyanin biosynthesis, Biosynthesis of secondary metabolites

MetaCyc

gentiodelphin biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

UDP-alpha-D-glucose:delphinidin-3,5-di-O-beta-D-glucoside 3'-O-glucosyltransferase

Isolated from the plant Gentiana triflora (clustered gentian).

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CAS REGISTRY NUMBER

COMMENTARY

380231-41-4

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

UDP-alpha-D-glucose + delphinidin 3-O-glucosyl-5-O-(6-O-caffeoylglucoside)

UDP + delphinidin 3-O,3'-O-di-beta-D-glucosyl-5-O-(6-O-caffeoyl-beta-D-glucoside)

Gentiana triflora

Q8H0F2

in vitro, 50.9% of the activity with delphinidin 3,5-diglucoside

657052

UDP-glucose + an anthocyanidin

UDP + an anthocyanidin 3'-O-beta-D-glucoside

Gentiana triflora

Q8H0F2

strict substrate specificity, 3'GT specifically glucosylates the 3'-hydroxy group of delphinidin-type anthocyanins containing glucose groups at the 3 and 5 positions and specifically uses UDP-glucose as the sugar donor, 3âGT strictly requires three hydroxy groups on the B-ring for its substrates

657052

UDP-glucose + delphinidin

UDP + delphinidin 3'-glucoside

Gentiana triflora

Q8H0F2

poor substrate, 3.3% of the activity with delphinidin 3,5-diglucoside

657052

UDP-glucose + delphinidin 3,5-di-O-beta-D-glucoside

UDP + delphinidin 3,5,7-tri-O-beta-D-glucoside

Gentiana triflora

Q8H0F2

3'GT glucosylates the 3'-hydroxy group of delphinidin 3,5-diglucoside, 2fold higher activity than with delphinidin 3-O-glucosyl-5-O-(6-O-caffeoylglucoside) as substrate

657052

UDP-glucose + delphinidin 3-glucoside

UDP + delphinidin 3,3'-diglucoside

Gentiana triflora

Q8H0F2

poor substrate, 2.9% of the activity with delphinidin 3,5-diglucoside

657052

additional information

2 entries

additional information

Gentiana triflora

Q8H0F2

key enzyme for blue anthocyanin biosynthesis, biosynthesis of gentiodelphin

657052

additional information

Gentiana triflora

Q8H0F2

no sugar donors: UDP-galactose, UDP-GlcUA, UDP-N-acetylgalactosamine, not: pelargonidin 3,5-diglucoside, cyanidin 3,5-diglucoside, dihydroflavonols, dihydrokaempferol, dihydroquercetin, dihydromyricetin, flavone, tricetin

657052

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

additional information

Gentiana triflora

Q8H0F2

key enzyme for blue anthocyanin biosynthesis, biosynthesis of gentiodelphin

657052

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

Al3+

80% inhibition

Co2+

69% inhibition

UDP

competitive inhibition

Zn2+

26% inhibition

additional information

Gentiana triflora

Q8H0F2

not inhibited by Mg2+, Ca2+, Mn2+, EDTA or EGTA

657052

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.12

delphinidin 3,5-diglucoside

Gentiana triflora

Q8H0F2

pH 8.5, 30Â°C, recombinant 3'GT

657052

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Ki VALUE [mM]

INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.76

UDP

Gentiana triflora

Q8H0F2

pH 8.5, 30Â°C, recombinant 3'GT

657052

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

8.5

assay at

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Gentiana triflora

var. japonica

657052

Q8H0F2

SwissProt

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

petal

Gentiana triflora

Q8H0F2

blue, from flowers at a pre-anthesis stage, 3'GT mRNA is abundant in petals at the first three developmental stages, but dramatically decreased in fully opened flowers

657052

brenda

additional information

Gentiana triflora

Q8H0F2

3'GT mRNA is barely detectable in leaves

657052

brenda

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

soluble

Gentiana triflora

Q8H0F2

recombinant 3'GT expressed in Escherichia coli JM105

657052

brenda

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

SEQUENCE

LOCALIZATION PREDICTION

The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).

Q8H0F2 pBLAST

ANGT_GENTR

Gentiana triflora

482

54041

Swiss-Prot

Show Sequence

other Location (Reliability: 5)

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

54037

Gentiana triflora

Q8H0F2

x * 55000, SDS-PAGE, x * 54037, sequence calculation

657052

55000

Gentiana triflora

Q8H0F2

x * 55000, SDS-PAGE, x * 54037, sequence calculation

657052

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Gentiana triflora

Q8H0F2

x * 55000, SDS-PAGE, x * 54037, sequence calculation

657052

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

native 3'GT from petals, recombinant 3'GT expressed in Escherichia coli JM105

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

expression in transgenic Petunia hybrida and in Escherichia coli JM105, sequencing

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APPLICATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

agriculture

Gentiana triflora

Q8H0F2

3'GT cDNA is a useful molecular tool for modification of flower color using genetic engineering, production of blue anthocyanins

657052

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

657052

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

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

Plant Physiol.

132

1652-1663

2003

Gentiana triflora (Q8H0F2)

12857844

brenda