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Information on EC 2.3.1.151 - 2,3',4,6-tetrahydroxybenzophenone synthase and Organism(s) Garcinia mangostana and UniProt Accession L7NCQ3

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EC Tree
IUBMB Comments
Involved in the biosynthesis of plant xanthones. Benzoyl-CoA can replace 3-hydroxybenzoyl-CoA (cf. EC 2.3.1.220, 2,4,6-trihydroxybenzophenone synthase).
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This record set is specific for:
Garcinia mangostana
UNIPROT: L7NCQ3
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The taxonomic range for the selected organisms is: Garcinia mangostana
The enzyme appears in selected viruses and cellular organisms
Synonyms
benzophenone synthase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2,3',4,6-Tetrahydroxybenzophenone synthase
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Synthase, benzophenone
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
decarboxylation
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Acyl group transfer
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intramolecular cyclization
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:3-hydroxybenzoyl-CoA malonyltransferase (decarboxylating, 2,3',4,6-tetrahydroxybenzophenone-forming)
Involved in the biosynthesis of plant xanthones. Benzoyl-CoA can replace 3-hydroxybenzoyl-CoA (cf. EC 2.3.1.220, 2,4,6-trihydroxybenzophenone synthase).
CAS REGISTRY NUMBER
COMMENTARY hide
175780-21-9
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 malonyl-CoA + 4-coumaroyl-CoA
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one + 2 CO2
show the reaction diagram
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-
?
3 malonyl-CoA + acetyl-CoA
4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
show the reaction diagram
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-
-
?
3 malonyl-CoA + benzoyl-CoA
4 CoA + 2,4,6-trihydroxybenzophenone + 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one + 4-hydroxy-6-phenyl-2H-pyran-2-one + 3 CO2
show the reaction diagram
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the recombinant enzyme produces 2,4,6-trihydroxybenzophenone as the predominant product with benzoyl CoA as substrate but also lactones of tetraketide and triketide type
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?
3 malonyl-CoA + cinnamoyl-CoA
4 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 3 CO2
show the reaction diagram
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-
-
?
3 malonyl-CoA + hexanoyl-CoA
4 CoA + 4-hydroxy-6-pentyl-2H-pyran-2-one + 5-hexanoyl-4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
show the reaction diagram
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?
3 malonyl-CoA + phenylacetyl-CoA
4 CoA + 4-hydroxy-6-(2-oxo-3-phenylpropyl)-2H-pyran-2-one + 6-benzyl-4-hydroxy-2H-pyran-2-one + 2-phenyl-1-(2,4,6-trihydroxyphenyl)ethanone + 3 CO2
show the reaction diagram
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?
3 malonyl-CoA + salicyl-CoA
4 CoA + 4-hydroxy-2H-chromen-2-one + 3 CO2
show the reaction diagram
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?
4 malonyl-CoA
4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
show the reaction diagram
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?
additional information
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00963
benzoyl-CoA
pH 7.0, 30°C, recombinant His-tagged BPS
0.01638
malonyl-CoA
pH 7.0, 30°C, recombinant His-tagged BPS
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.049
benzoyl-CoA
pH 7.0, 30°C, recombinant His-tagged BPS
0.058
malonyl-CoA
pH 7.0, 30°C, recombinant His-tagged BPS
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
recombinant His-tagged BPS
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
recombinant His-tagged BPS
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.97
sequence calculation
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
expression of GmBPS in fruit pericarp from an early stage
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
Garcinia mangostana BPS is an enzyme in the family of type III polyketide synthases and shows an amino acid sequence identity of 77-78% with other plant BPSs belonging to the same family (Clusiaceae). The three BPSs from the xanthone-rich Clusiaceae plants, Garcinia mangostana, Hypericum androsaemum, and Hypericum perforatum, suggest a close evolutionary relationship among these enzymes
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
TBSYN_GARMA
391
0
42712
Swiss-Prot
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation
45618
2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation
88000
His-tagged enzyme, gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A257G
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme
G339S
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme
G339V
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme
T133L
site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His-tagged BPS from Escherichia coli
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic tree, expression of C-terminally His-tagged BPS in Escherichia coli
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nualkaew, N.; Morita, H.; Shimokawa, Y.; Kinjo, K.; Kushiro, T.; De-Eknamkul, W.; Ebizuka, Y.; Abe, I.
Benzophenone synthase from Garcinia mangostana L. pericarps
Phytochemistry
77
60-69
2012
Garcinia mangostana (L7NCQ3), Garcinia mangostana
Manually annotated by BRENDA team