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Literature summary extracted from

  • Stewart, C.; Woods, K.; Macias, G.; Allan, A.C.; Hellens, R.P.; Noel, J.P.
    Molecular architectures of benzoic acid-specific type III polyketide synthases (2017), Acta Crystallogr. Sect. D, 73, 1007-1019 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.3.1.74 hanging-drop vapor-diffusion method using buffered protein solutions (10-15 mg/ml) mixed with equal volumes of the reservoir solution and incubated at 4°C. Crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica Malus domestica
2.3.1.74 hanging-drop vapor-diffusion method, incubation at 4°C. Crystal structures of biphenyl synthase from Malusx02domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase: chalcone synthase from Malus domestica. Both biphenyl synthase and benzophenone synthase contain mutations that reshape their active-site cavities to prevent the binding of 4-coumaroyl-CoA and to favor the binding of small hydrophobic substrates. The active-site cavities of biphenyl synthase and benzophenone synthase also contain a novel pocket associated with their chain-elongation and cyclization reactions Malus domestica
2.3.1.177 hanging-drop vapor-diffusion method using buffered protein solutions (10-15 mg/ml) mixed with equal volumes of the reservoir solution and incubated at 4°C. Crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica Malus domestica
2.3.1.177 hanging-drop vapor-diffusion method, incubation at 4°C. Crystal structures of biphenyl synthase from Malusx02domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase: chalcone synthase from Malus domestica. Both biphenyl synthase and benzophenone synthase contain mutations that reshape their active-site cavities to prevent the binding of 4-coumaroyl-CoA and to favor the binding of small hydrophobic substrates. The active-site cavities of biphenyl synthase and benzophenone synthase also contain a novel pocket associated with their chain-elongation and cyclization reactions Malus domestica
2.3.1.220 hanging-drop vapor-diffusion method using buffered protein solutions (10-15 mg/ml) mixed with equal volumes of the reservoir solution and incubated at 4°C. Crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica Hypericum androsaemum
2.3.1.220 hanging-drop vapor-diffusion method, incubation at 4°C. Crystal structures of biphenyl synthase from Malusx02domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase: chalcone synthase from Malus domestica. Both biphenyl synthase and benzophenone synthase contain mutations that reshape their active-site cavities to prevent the binding of 4-coumaroyl-CoA and to favor the binding of small hydrophobic substrates. The active-site cavities of biphenyl synthase and benzophenone synthase also contain a novel pocket associated with their chain-elongation and cyclization reactions Hypericum androsaemum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.74 0.0128
-
 malonyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.74 0.0179
-
 4-coumaroyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.0005
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.00068
-
 malonyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.0008
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.0041
-
 malonyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.0068
-
 malonyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.220 0.0013
-
 benzoyl-CoA pH 7.0, 37°C Hypericum androsaemum
2.3.1.220 0.0028
-
 malonyl-CoA pH 7.0, 37°C Hypericum androsaemum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.74 3 malonyl-CoA + 4-coumaroyl-CoA Malus domestica
-
 4 CoA + naringenin chalcone + 3 CO2
-
 ?
2.3.1.74 3 malonyl-CoA + benzoyl-CoA Malus domestica
-
 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
 ?
2.3.1.177 3 malonyl-CoA + benzoyl-CoA Malus domestica
-
 4 CoA + 3,5-dihydroxybiphenyl + 4 CO2
-
 ?
2.3.1.220 3 malonyl-CoA + benzoyl-CoA Hypericum androsaemum
-
 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.74 Malus domestica K9MUA0
-
-
2.3.1.177 Malus domestica K9MS05
-
-
2.3.1.177 Malus domestica K9MST3
-
-
2.3.1.220 Hypericum androsaemum Q8SAS8
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.74 3 malonyl-CoA + 4-coumaroyl-CoA
-
 Malus domestica 4 CoA + naringenin chalcone + 3 CO2
-
 ?
2.3.1.74 3 malonyl-CoA + benzoyl-CoA
-
 Malus domestica 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
 ?
2.3.1.177 3 malonyl-CoA + benzoyl-CoA
-
 Malus domestica 4 CoA + 3,5-dihydroxybiphenyl + 4 CO2
-
 ?
2.3.1.220 3 malonyl-CoA + benzoyl-CoA
-
 Hypericum androsaemum 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.74 CHS2 chalcone synthase
-
 Malus domestica
2.3.1.74 MdCHS2
-
 Malus domestica
2.3.1.177 BIS1 biphenyl synthase
-
 Malus domestica
2.3.1.177 BIS3 biphenyl synthase
-
 Malus domestica
2.3.1.177 MdBIS1
-
 Malus domestica
2.3.1.177 MdBIS3
-
 Malus domestica
2.3.1.220 benzophenone synthase
-
 Hypericum androsaemum
2.3.1.220 HaBPS
-
 Hypericum androsaemum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.74 0.02
-
 4-coumaroyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.74 0.0202
-
 4-coumaroyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.135
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 0.283
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.220 0.018
-
 benzoyl-CoA pH 7.0, 37°C Hypericum androsaemum
2.3.1.220 0.0183
-
 benzoyl-CoA pH 7.0, 37°C Hypericum androsaemum

General Information

EC Number General Information Comment Organism
2.3.1.74 evolution crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica. The results illuminate structural determinants of benzoic acid-specific type III PKSs and expand the understanding of the evolution of specialized metabolic pathways in plants Malus domestica
2.3.1.177 evolution crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica. The results illuminate structural determinants of benzoic acid-specific type III PKSs and expand the understanding of the evolution of specialized metabolic pathways in plants Malus domestica
2.3.1.220 evolution crystal structures of biphenyl synthase from Malus domestica and benzophenone synthase from Hypericum androsaemum are compared with the structure of an archetypal type III polyketide synthase - chalcone synthase from Malus domestica. The results illuminate structural determinants of benzoic acid-specific type III PKSs and expand the understanding of the evolution of specialized metabolic pathways in plants Hypericum androsaemum

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.3.1.74 1.1
-
 4-coumaroyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.74 1.117
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 270
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 350
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.177 353.75
-
 benzoyl-CoA pH 7.0, 37°C Malus domestica
2.3.1.220 14
-
 benzoyl-CoA pH 7.0, 37°C Hypericum androsaemum