Information on EC 2.3.1.177 - 3,5-dihydroxybiphenyl synthase

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The expected taxonomic range for this enzyme is: Maleae

EC NUMBER
COMMENTARY hide
2.3.1.177
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RECOMMENDED NAME
GeneOntology No.
3,5-dihydroxybiphenyl synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3 malonyl-CoA + benzoyl-CoA = 4 CoA + 3,5-dihydroxybiphenyl + 4 CO2
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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aldol condensation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
aucuparin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:benzoyl-CoA malonyltransferase
A polyketide synthase that is involved in the production of the phytoalexin aucuparin. 2-Hydroxybenzoyl-CoA can also act as substrate but it leads to the derailment product 4-hydroxycoumarin (cf. EC 2.3.1.208, 4-hydroxycoumarin synthase) [2]. This enzyme uses the same starter substrate as EC 2.3.1.151, benzophenone synthase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-hydroxybenzoyl-CoA + malonyl-CoA
4-hydroxycoumarin + CoA + CO2
show the reaction diagram
3 malonyl-CoA + benzoyl-CoA
4 CoA + 3,5-dihydroxybiphenyl + 4 CO2
show the reaction diagram
malonyl-CoA + 2-hydroxybenzoyl-CoA
CoA + 2-hydroxybenzoyltriacetic acid lactone + CO2
show the reaction diagram
malonyl-CoA + 3-hydroxybenzoyl-CoA
CoA + 3-hydroxycoumarin
show the reaction diagram
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8% of the activity with benzoyl-CoA without acidification, 22% of the activity with benzoyl-CoA with acidification
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?
malonyl-CoA + 3-hydroxybenzoyl-CoA
CoA + ? + CO2
show the reaction diagram
68% of the activity with benzoyl-CoA
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?
malonyl-CoA + benzoyl-CoA
CoA + 3,5-dihydroxybiphenyl + CO2
show the reaction diagram
malonyl-CoA + isobutyryl-CoA
CoA + ?
show the reaction diagram
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5% of the activity with benzoyl-CoA without acidification, 15% of the activity with benzoyl-CoA with acidification
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3 malonyl-CoA + benzoyl-CoA
4 CoA + 3,5-dihydroxybiphenyl + 4 CO2
show the reaction diagram
malonyl-CoA + benzoyl-CoA
CoA + 3,5-dihydroxybiphenyl + CO2
show the reaction diagram
additional information
?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
benzoyl-CoA
H2FL89, H2FL90, H2FL91, JQ390521
benzoyl-CoA causes inhibition of BIS2 activity at concentrations above 0.015 mM; benzoyl-CoA causes inhibition of BIS3 activity at concentrations above 0.015 mM; benzoyl-CoA causes inhibition of BIS4 activity at concentrations above 0.015 mM
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
DTT
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stimulates
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0008 - 0.0032
2-hydroxybenzoyl-CoA
0.0007 - 0.7
benzoyl-CoA
0.0062 - 6.2
malonyl-CoA
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0045 - 0.037
2-hydroxybenzoyl-CoA
0.00717 - 0.017
benzoyl-CoA
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5.625 - 12.72
2-hydroxybenzoyl-CoA
10.18 - 10.99
benzoyl-CoA
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
7 - 7.5
H2FL89, H2FL90, H2FL91, JQ390521
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35 - 40
H2FL89, H2FL90, H2FL91, JQ390521
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
H2FL89, H2FL90, H2FL91, JQ390521
very low expression of BIS2
Manually annotated by BRENDA team
H2FL89, H2FL90, H2FL91, JQ390521
Erwinia amylovora infected; Erwinia amylovora infected; Erwinia amylovora infected, high expression levels of BIS3
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
H2FL89, H2FL90, H2FL91, JQ390521
x * 43000, recombinant His-tagged BIS enzyme, SDS-PAGE; x * 43000, recombinant His-tagged BIS enzyme, SDS-PAGE; x * 43000, recombinant His-tagged BIS enzyme, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified by affinity chromatography on a nickel-nitrilotriacetic acid (Ni-NTA) agarose matrix; purified by affinity chromatography on a nickel-nitrilotriacetic acid (Ni-NTA) agarose matrix
recombinant N-terminally His6-tagged BIS2, BIS3, and BIS4 from Escherichia coli; recombinant N-terminally His6-tagged BIS3 from Escherichia coli; recombinant N-terminally His6-tagged BIS4 from Escherichia coli
H2FL89, H2FL90, H2FL91, JQ390521
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli as N-terminally 6His-tagged protein; expressed in Escherichia coli as N-terminally 6His-tagged protein
gene MdBIS1, DNA and amino acid sequence determination and analysis, phylogenetic tree, the BIS1 cDNA cloned from cv. Holsteiner Cox contains an early stop codon atposition 211 to 213 and does not yield a functional enzyme; gene MdBIS2, DNA and amino acid sequence determination and analysis, phylogenetic tree, functional expression of N-terminally His6-tagged BIS2 in Escherichia coli; gene MdBIS4, DNA and amino acid sequence determination and analysis, phylogenetic tree, functional expression of N-terminally His6-tagged BIS4 in Escherichia coli; genes MdBIS3, DNA and amino acid sequence determination and analysis, phylogenetic tree, functional expression of N-terminally His6-tagged BIS3 in Escherichia coli
H2FL89, H2FL90, H2FL91, JQ390521
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
addition of yeast extract to the cell cultures results in a burst of reactive oxygen species, H2O2 and O2-, followed by transcriptional activation of the biphenyl synthase 1 gene BIS1. Endogenous generation of H2O2, by superoxide dismutase, rather than that of O2- is akey factor in YE-induced accumulation of biphenyl phytoalexins in cell cultures of Sorbus aucuparia
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BIS is only expressed when plant is infected with microorganisms
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infection with Erwinia amylovora induces the enzyme; infection with Erwinia amylovora induces the enzyme. In cell cultures of apple cultivar Cox Orange, expression of BIS2 gene is observed after the addition of an autoclaved Erwinia amylovora suspension, BIS3 protein is accumulated in the transition zone of stems in the parenchyma of the bark at the junctions between neighboring cortical parenchyma cells; the BIS3 gene is reduced in response to inoculation with Erwinia amylovora in stems of cv. Holsteiner Cox with highest transcript levels in the transition zone between necrotic and healthy tissues. In cell cultures of apple cultivar Cox Orange, expression of BIS3 gene is observed after the addition of an autoclaved Erwinia amylovora suspension, BIS3 protein is accumulated in the transition zone of stems in the parenchyma of the bark at the junctions between neighboring cortical parenchyma cells
H2FL89, H2FL90, H2FL91, JQ390521
the enzyme is induced by elicitors