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Literature summary for 2.3.1.208 extracted from
- A novel 4-hydroxycoumarin biosynthetic pathway (2010), Plant Mol. Biol., 72, 17-25.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| isozyme BIS2, cDNA and amino acid sequence determination and analysis, recombinant expression of the His-tagged isozyme | Sorbus aucuparia |
| isozyme BIS3, cDNA and amino acid sequence determination and analysis, recombinant expression of the His-tagged isozyme | Sorbus aucuparia |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0008 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS1 | Sorbus aucuparia |  |
| 0.0023 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS2 | Sorbus aucuparia | |
| 0.0032 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS3 | Sorbus aucuparia | |
| 0.0062 | - |
malonyl-CoA | pH 6.5-7.0, 35°C, BIS1 | Sorbus aucuparia | |
| 0.01 | - |
malonyl-CoA | pH 6.5-7.0, 35°C, BIS2 | Sorbus aucuparia | |
| 0.0101 | - |
malonyl-CoA | pH 6.5-7.0, 35°C, BIS3 | Sorbus aucuparia | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 43100 | - |
x * 43100, about, BIS2, sequence calculation | Sorbus aucuparia |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| malonyl-CoA + 2-hydroxybenzoyl-CoA | Sorbus aucuparia | - |
2 CoA + 4-hydroxycoumarin + CO2 | - |
? | |
| malonyl-CoA + 3-hydroxybenzoyl-CoA | Sorbus aucuparia | - |
2 CoA + 2-oxabicyclo[4.3.1]deca-1(10),6,8-triene-3,5-dione + CO2 | - |
? | |
| 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 | ? | - |
? | |
| 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
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Sorbus aucuparia | - |
isozyme BIS1 | - |
| Sorbus aucuparia | D2DRC4 | BIS2; isozyme BIS2 | - |
| Sorbus aucuparia | D2DRC5 | BIS3; isozyme BIS3 | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant His-tagged BIS2 by nickel affinity chromatography | Sorbus aucuparia |
| recombinant His-tagged BIS3 by nickel affinity chromatography | Sorbus aucuparia |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| cell culture | elicitor-treated | Sorbus aucuparia | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| malonyl-CoA + 2-hydroxybenzoyl-CoA | - |
Sorbus aucuparia | 2 CoA + 4-hydroxycoumarin + CO2 | - |
? | |
| malonyl-CoA + 3-hydroxybenzoyl-CoA | - |
Sorbus aucuparia | 2 CoA + 2-oxabicyclo[4.3.1]deca-1(10),6,8-triene-3,5-dione + CO2 | - |
? | |
| 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 | ? | - |
? | |
| 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 | ? | - |
? | |
| 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
| Subunits | Comment | Organism |
|---|---|---|
| ? | x * 4300, about, BIS3, sequence calculation | Sorbus aucuparia |
| ? | x * 43100, about, BIS2, sequence calculation | Sorbus aucuparia |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| BIS1 | - |
Sorbus aucuparia |
| BIS2 | - |
Sorbus aucuparia |
| BIS3 | - |
Sorbus aucuparia |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 35 | - |
- |
Sorbus aucuparia |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0045 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS1 | Sorbus aucuparia | |
| 0.029 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS2 | Sorbus aucuparia | |
| 0.037 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS3 | Sorbus aucuparia | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 6.5 | 7 | - |
Sorbus aucuparia |
pI Value
| Organism | Comment | pI Value Maximum | pI Value |
|---|---|---|---|
| Sorbus aucuparia | BIS2, sequence calculation | - |
5.45 |
| Sorbus aucuparia | BIS3, sequence calculation | - |
6.42 |
Expression
| Organism | Comment | Expression |
|---|---|---|
| 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 |
| 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
| General Information | Comment | Organism |
|---|---|---|
| additional information | the isozyme contains the Cys-His-Asn catalytic triad conserved in type III PKSs | Sorbus aucuparia |
| 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]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 5.625 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS1 | Sorbus aucuparia | |
| 11.49 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS3 | Sorbus aucuparia | |
| 12.72 | - |
2-hydroxybenzoyl-CoA | pH 6.5-7.0, 35°C, BIS2 | Sorbus aucuparia | |
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