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Information on EC 2.3.1.177 - 3,5-dihydroxybiphenyl synthase and Organism(s) Sorbus aucuparia and UniProt Accession Q27Z07

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EC Tree
IUBMB Comments
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) . This enzyme uses the same starter substrate as EC 2.3.1.151, benzophenone synthase.
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This record set is specific for:
Sorbus aucuparia
UNIPROT: Q27Z07
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The taxonomic range for the selected organisms is: Sorbus aucuparia
The enzyme appears in selected viruses and cellular organisms
Synonyms
biphenyl synthase, pcbis2, mdbis1, pcbis1, mdbis3, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biphenyl synthase
enzyme belongs to the type III polyketide synthases
BIS
enzyme belongs to the type III polyketide synthases
biphenyl synthase
BIS2
enzyme belongs to the type III polyketide synthases, prefering 2-hydroxybenzoyl-CoA as a starter molecule instead of benzoyl-CoA
BIS3
enzyme belongs to the type III polyketide synthases, prefering 2-hydroxybenzoyl-CoA as a starter molecule instead of benzoyl-CoA
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aldol condensation
-
-
Acyl group transfer
-
-
PATHWAY SOURCE
PATHWAYS
-
-
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.
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
-
-
-
?
malonyl-CoA + 2-hydroxybenzoyl-CoA
CoA + 2-hydroxybenzoyltriacetic acid lactone + CO2
show the reaction diagram
52% of the activity with benzoyl-CoA
-
-
?
malonyl-CoA + 3-hydroxybenzoyl-CoA
CoA + ? + CO2
show the reaction diagram
68% of the activity with benzoyl-CoA
-
-
?
malonyl-CoA + benzoyl-CoA
CoA + 3,5-dihydroxybiphenyl + CO2
show the reaction diagram
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
-
11% of the activity with benzoyl-CoA without acidification, 86% of the activity with benzoyl-CoA with acidification
derailment product
-
?
malonyl-CoA + 3-hydroxybenzoyl-CoA
CoA + 3-hydroxycoumarin
show the reaction diagram
-
8% of the activity with benzoyl-CoA without acidification, 22% of the activity with benzoyl-CoA with acidification
-
-
?
malonyl-CoA + benzoyl-CoA
CoA + 3,5-dihydroxybiphenyl + CO2
show the reaction diagram
malonyl-CoA + isobutyryl-CoA
CoA + ?
show the reaction diagram
-
5% of the activity with benzoyl-CoA without acidification, 15% of the activity with benzoyl-CoA with acidification
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
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
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
DTT
-
stimulates
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0008
2-hydroxybenzoyl-CoA
-
0.0007 - 0.7
benzoyl-CoA
0.0062 - 6.2
malonyl-CoA
0.0023 - 0.0032
2-hydroxybenzoyl-CoA
0.0014 - 0.0016
benzoyl-CoA
0.01 - 0.0101
malonyl-CoA
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0045
2-hydroxybenzoyl-CoA
-
0.00717 - 0.0072
benzoyl-CoA
0.02933 - 0.037
2-hydroxybenzoyl-CoA
0.01483 - 0.017
benzoyl-CoA
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5.625
2-hydroxybenzoyl-CoA
-
10.18
benzoyl-CoA
-
11.49 - 12.72
2-hydroxybenzoyl-CoA
10.63 - 10.99
benzoyl-CoA
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
detection of enzyme in discrete globules and at the surface of cells treated with an suspension of Erwinia amylovora
Manually annotated by BRENDA team
fluorescent reporter fusions are localized to the cytoplasm of Nicotiana benthamiana leaf epidermis cells
Manually annotated by BRENDA team
detection of enzyme in discrete globules and at the surface of cells treated with an suspension of Erwinia amylovora
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
BIS is the key enzyme of biphenyl metabolism, producing for instance 3,5-dihydroxybiphenyl which is the precursor of the phytoalexins of the Maloideae.
evolution
-
the type-III polyketide synthase biphenyl synthase is encoded by a gene family, members of which are differentially regulated
metabolism
physiological function
-
biphenyls, whose biosynthesis involves the biphenyl synthase, and dibenzofurans are the phytoalexins of the Pyrinae, corresponding to the Maloideae, a subfamily of the plant family Rosaceae. Occurrence of biphenyl phytoalexins in species of the Pyrinae, overview
additional information
-
biphenyls exhibit stronger antibacterial activity than structurally related dibenzofurans do, occurrence of dibenzofuran phytoalexins in species of the Pyrinae, overview
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
BIPS1_SORAU
390
0
43014
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified by affinity chromatography on a nickel-nitrilotriacetic acid (Ni-NTA) agarose matrix
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli as N-terminally 6His-tagged protein
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transient induction by treatment with an elicitor preparation from the scab-causing fungus, Venturia inaequalis. Expression of BIS1 is strongly upregulated within 3 h, reaches a maximum at 6 h and decreases thereafter continuously
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
-
BIS is only expressed when plant is infected with microorganisms
-
the enzyme is induced by elicitors
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Liu, B.; Beuerle, T.; Klundt, T.; Beerhues, L.
Biphenyl synthase from yeast-extract-treated cell cultures of Sorbus aucuparia
Planta
218
492-496
2004
Sorbus aucuparia
Manually annotated by BRENDA team
Liu, B.; Raeth, T.; Beuerle, T.; Beerhues, L.
Biphenyl synthase, a novel type III polyketide synthase
Planta
225
1495-1503
2007
Sorbus aucuparia (Q27Z07), Sorbus aucuparia
Manually annotated by BRENDA team
Beerhues, L.; Liu, B.; Raeth, T.; Klundt, T.; Beuerle, T.; Bocola, M.
Benzoic acid-specific type III polyketide synthases
ACS Symp. Ser.
955
97-108
2007
Sorbus aucuparia
-
Manually annotated by BRENDA team
Beerhues, L.; Liu, B.
Biosynthesis of biphenyls and benzophenones-evolution of benzoic acid-specific type III polyketide synthases in plants
Phytochemistry
70
1719-1727
2009
Sorbus aucuparia
Manually annotated by BRENDA team
Liu, B.; Raeth, T.; Beuerle, T.; Beerhues, L.
A novel 4-hydroxycoumarin biosynthetic pathway
Plant Mol. Biol.
72
17-25
2010
Sorbus aucuparia (D2DRC4), Sorbus aucuparia (D2DRC5), Sorbus aucuparia (Q27Z07), Sorbus aucuparia
Manually annotated by BRENDA team
Chizzali, C.; Beerhues, L.
Phytoalexins of the pyrinae: biphenyls and dibenzofurans
Beilstein J. Org. Chem.
8
613-620
2012
Aronia arbutifolia, Chaenomeles cathayensis, Chaenomeles japonica, Malus domestica, Malus sieversii, Malus sylvestris, Photinia glabra, Pyrus communis, Rhaphiolepis bibas, Rhaphiolepis umbellata, Sorbus aucuparia
Manually annotated by BRENDA team
Qiu, X.; Lei, C.; Huang, L.; Li, X.; Hao, H.; Du, Z.; Wang, H.; Ye, H.; Beerhues, L.; Liu, B.
Endogenous hydrogen peroxide is a key factor in the yeast extract-induced activation of biphenyl biosynthesis in cell cultures of Sorbus aucuparia
Planta
235
217-223
2012
Sorbus aucuparia
Manually annotated by BRENDA team
Reckwell, D.; Haensch, R.; Schulze, J.; Beerhues, L.
Immunolocalization of biphenyl synthase in elicitor-treated cell cultures of Sorbus aucuparia
Acta Hortic.
1056
307-311
2014
Sorbus aucuparia (Q27Z07)
-
Manually annotated by BRENDA team
Khalil, M.N.; Brandt, W.; Beuerle, T.; Reckwell, D.; Groeneveld, J.; Haensch, R.; Gaid, M.M.; Liu, B.; Beerhues, L.
O-Methyltransferases involved in biphenyl and dibenzofuran biosynthesis
Plant J.
83
263-276
2015
Sorbus aucuparia (Q27Z07), Sorbus aucuparia
Manually annotated by BRENDA team