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Literature summary extracted from

  • Liu, B.; Raeth, T.; Beuerle, T.; Beerhues, L.
    A novel 4-hydroxycoumarin biosynthetic pathway (2010), Plant Mol. Biol., 72, 17-25.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.177 expressed in Escherichia coli as N-terminally 6His-tagged protein Sorbus aucuparia
2.3.1.208 isozyme BIS2, cDNA and amino acid sequence determination and analysis, recombinant expression of the His-tagged isozyme Sorbus aucuparia
2.3.1.208 isozyme BIS3, cDNA and amino acid sequence determination and analysis, recombinant expression of the His-tagged isozyme Sorbus aucuparia

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.177 0.0007
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0008
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0014
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0016
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0023
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0032
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0062
-
 malonyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.01
-
 malonyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.0101
-
 malonyl-CoA
-
 Sorbus aucuparia
2.3.1.208 0.0008
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS1 Sorbus aucuparia
2.3.1.208 0.0023
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS2 Sorbus aucuparia
2.3.1.208 0.0032
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS3 Sorbus aucuparia
2.3.1.208 0.0062
-
 malonyl-CoA pH 6.5-7.0, 35°C, BIS1 Sorbus aucuparia
2.3.1.208 0.01
-
 malonyl-CoA pH 6.5-7.0, 35°C, BIS2 Sorbus aucuparia
2.3.1.208 0.0101
-
 malonyl-CoA pH 6.5-7.0, 35°C, BIS3 Sorbus aucuparia

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.177 43000
-
-
 Sorbus aucuparia
2.3.1.177 43100
-
-
 Sorbus aucuparia
2.3.1.208 43100
-
 x * 43100, about, BIS2, sequence calculation Sorbus aucuparia

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.208 malonyl-CoA + 2-hydroxybenzoyl-CoA Sorbus aucuparia
-
 2 CoA + 4-hydroxycoumarin + CO2
-
 ?
2.3.1.208 malonyl-CoA + 3-hydroxybenzoyl-CoA Sorbus aucuparia
-
 2 CoA + 2-oxabicyclo[4.3.1]deca-1(10),6,8-triene-3,5-dione + CO2
-
 ?
2.3.1.208 additional information Sorbus aucuparia biphenyl synthase isozyme BIS1, in contrast to isozymes BIS2 and BIS3, does not prefer 2-hydroxybenzoyl (salicyl)-CoA as a starter substrat, but also catalyzes a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin ?
-
 ?
2.3.1.208 additional information Sorbus aucuparia in contrast to isozyme BIS1, biphenyl synthase isoenzymes BIS2 and BIS3 prefer ortho-hydroxybenzoyl (salicyl)-CoA as a starter substrate and catalyze a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.177 Sorbus aucuparia D2DRC4
-
-
2.3.1.177 Sorbus aucuparia D2DRC5
-
-
2.3.1.177 Sorbus aucuparia Q27Z07
-
-
2.3.1.208 Sorbus aucuparia
-
 isozyme BIS1
-
2.3.1.208 Sorbus aucuparia D2DRC4 BIS2; isozyme BIS2
-
2.3.1.208 Sorbus aucuparia D2DRC5 BIS3; isozyme BIS3
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.177 purified by affinity chromatography on a nickel-nitrilotriacetic acid (Ni-NTA) agarose matrix Sorbus aucuparia
2.3.1.208 recombinant His-tagged BIS2 by nickel affinity chromatography Sorbus aucuparia
2.3.1.208 recombinant His-tagged BIS3 by nickel affinity chromatography Sorbus aucuparia

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.208 cell culture elicitor-treated Sorbus aucuparia
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.177 2-hydroxybenzoyl-CoA + malonyl-CoA
-
 Sorbus aucuparia 4-hydroxycoumarin + CoA + CO2
-
 ?
2.3.1.177 malonyl-CoA + benzoyl-CoA
-
 Sorbus aucuparia CoA + 3,5-dihydroxybiphenyl + CO2
-
 ?
2.3.1.208 malonyl-CoA + 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia 2 CoA + 4-hydroxycoumarin + CO2
-
 ?
2.3.1.208 malonyl-CoA + 3-hydroxybenzoyl-CoA
-
 Sorbus aucuparia 2 CoA + 2-oxabicyclo[4.3.1]deca-1(10),6,8-triene-3,5-dione + CO2
-
 ?
2.3.1.208 additional information biphenyl synthase isozyme BIS1, in contrast to isozymes BIS2 and BIS3, does not prefer 2-hydroxybenzoyl (salicyl)-CoA as a starter substrat, but also catalyzes a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin Sorbus aucuparia ?
-
 ?
2.3.1.208 additional information in contrast to isozyme BIS1, biphenyl synthase isoenzymes BIS2 and BIS3 prefer ortho-hydroxybenzoyl (salicyl)-CoA as a starter substrate and catalyze a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin Sorbus aucuparia ?
-
 ?
2.3.1.208 additional information substrate specificities of BIS isoenzymes from cell cultures, overview. The bifunctional enzyme also forms 3,5-dihydroxybiphenyl from malonyl-CoA and benzoyl-CoA, reaction of biphenyl synthase, EC 2.3.1.177. When benzoyl-CoA is replaced with salicyl-CoA as a starter substrate, the enzyme catalyzes a single decarboxylative condensation reaction with malonyl-CoA to form a diketide intermediate which undergoes intramolecular cyclization by nucleophilic attack of the phenol group on the CoA- or cysteine-tethered C-1 thioester, yielding 4-hydroxycoumarin after enolization. No activity with 4-hydroxybenzoyl-CoA, cinnamoyl-CoA, 2-coumaroyl-CoA, 3-coumaroyl-CoA, 4-coumaroyl-CoA, and acetyl-CoA or with free salicylic acid or 2-coumaric acid Sorbus aucuparia ?
-
 ?

Subunits

EC Number Subunits Comment Organism
2.3.1.208 ? x * 4300, about, BIS3, sequence calculation Sorbus aucuparia
2.3.1.208 ? x * 43100, about, BIS2, sequence calculation Sorbus aucuparia

Synonyms

EC Number Synonyms Comment Organism
2.3.1.177 biphenyl synthase enzyme belongs to the type III polyketide synthases Sorbus aucuparia
2.3.1.177 BIS enzyme belongs to the type III polyketide synthases Sorbus aucuparia
2.3.1.177 BIS1
-
 Sorbus aucuparia
2.3.1.177 BIS2 enzyme belongs to the type III polyketide synthases, prefering 2-hydroxybenzoyl-CoA as a starter molecule instead of benzoyl-CoA Sorbus aucuparia
2.3.1.177 BIS3 enzyme belongs to the type III polyketide synthases, prefering 2-hydroxybenzoyl-CoA as a starter molecule instead of benzoyl-CoA Sorbus aucuparia
2.3.1.208 BIS1
-
 Sorbus aucuparia
2.3.1.208 BIS2
-
 Sorbus aucuparia
2.3.1.208 BIS3
-
 Sorbus aucuparia

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.177 35
-
-
 Sorbus aucuparia
2.3.1.208 35
-
-
 Sorbus aucuparia

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.177 0.0045
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.00717
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.01483
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.017
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.02933
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 0.037
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.208 0.0045
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS1 Sorbus aucuparia
2.3.1.208 0.029
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS2 Sorbus aucuparia
2.3.1.208 0.037
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS3 Sorbus aucuparia

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.177 6.5 7
-
 Sorbus aucuparia
2.3.1.208 6.5 7
-
 Sorbus aucuparia

pI Value

EC Number Organism Comment pI Value Maximum pI Value
2.3.1.177 Sorbus aucuparia
-
-
 5.45
2.3.1.177 Sorbus aucuparia
-
-
 6.42
2.3.1.208 Sorbus aucuparia BIS2, sequence calculation
-
 5.45
2.3.1.208 Sorbus aucuparia BIS3, sequence calculation
-
 6.42

Expression

EC Number Organism Comment Expression
2.3.1.208 Sorbus aucuparia elicitor-treated cell cultures of Sorbus aucuparia form 4-hydroxycoumarin when fed with the N-acetylcysteamine thioester of salicylic acid (salicyl-NAC), elicitors induce BIS2, expression profile, overview up
2.3.1.208 Sorbus aucuparia elicitor-treated cell cultures of Sorbus aucuparia form 4-hydroxycoumarin when fed with the N-acetylcysteamine thioester of salicylic acid (salicyl-NAC), elicitors induce BIS3, expression profile, overview up

General Information

EC Number General Information Comment Organism
2.3.1.177 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. Sorbus aucuparia
2.3.1.208 additional information the isozyme contains the Cys-His-Asn catalytic triad conserved in type III PKSs Sorbus aucuparia
2.3.1.208 physiological function elicitor-treated cell cultures of Sorbus aucuparia form 4-hydroxycoumarin when fed with the N-acetylcysteamine thioester of salicylic acid (salicyl-NAC) Sorbus aucuparia

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.3.1.177 5.625
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 10.18
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 10.63
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 10.99
-
 benzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 11.49
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.177 12.72
-
 2-hydroxybenzoyl-CoA
-
 Sorbus aucuparia
2.3.1.208 5.625
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS1 Sorbus aucuparia
2.3.1.208 11.49
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS3 Sorbus aucuparia
2.3.1.208 12.72
-
 2-hydroxybenzoyl-CoA pH 6.5-7.0, 35°C, BIS2 Sorbus aucuparia