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Literature summary extracted from

  • Nualkaew, N.; Morita, H.; Shimokawa, Y.; Kinjo, K.; Kushiro, T.; De-Eknamkul, W.; Ebizuka, Y.; Abe, I.
    Benzophenone synthase from Garcinia mangostana L. pericarps (2012), Phytochemistry, 77, 60-69.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.151 DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic tree, expression of C-terminally His-tagged BPS in Escherichia coli Garcinia mangostana
2.3.1.220 DNA and amin acid sequence determination and analysis, sequence comparison and phylogenetic tree Garcinia mangostana

Protein Variants

EC Number Protein Variants Comment Organism
2.3.1.151 A257G site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme Garcinia mangostana
2.3.1.151 G339S site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme Garcinia mangostana
2.3.1.151 G339V site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme Garcinia mangostana
2.3.1.151 T133L site-directed mutagenesis, the mutant shows an altered product pattern compared to the wild-type enzyme Garcinia mangostana
2.3.1.220 A257G site-directed mutagenesis, altered substrate entrance in the active site structure compared to the wild-type enzyme. The mutant A257G gives similar enzyme products as the wild type with both benzoyl-CoA and 4-coumaroyl-CoA Garcinia mangostana
2.3.1.220 G339S site-directed mutagenesis, altered substrate entrance in the active site structure compared to the wild-type enzyme. The mutant G339S yields high amounts of both benzophenone and triketide lactone type with benzoyl-CoA but shows no activity for 4-coumaroyl-CoA Garcinia mangostana
2.3.1.220 G339V site-directed mutagenesis, altered substrate entrance in the active site structure compared to the wild-type enzyme. The mutant shows no activity with either benzoyl-CoA or 4-coumaroyl-CoA Garcinia mangostana
2.3.1.220 additional information homology model of wild-type GmBPS and GmBPS mutants A257G, T133L, G339V, and G339S, active-site architectures by surface models and substrate entrances, overview Garcinia mangostana
2.3.1.220 T133L site-directed mutagenesis, altered substrate entrance in the active site structure compared to the wild-type enzyme. With benzoyl-CoA as a starter, the T133L mutant yields triketide lactone as the major enzymatic product Garcinia mangostana

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.151 0.00963
-
benzoyl-CoA pH 7.0, 30°C, recombinant His-tagged BPS Garcinia mangostana
2.3.1.151 0.01638
-
malonyl-CoA pH 7.0, 30°C, recombinant His-tagged BPS Garcinia mangostana
2.3.1.220 0.00965
-
benzoyl-CoA pH 7.0, 30°C Garcinia mangostana
2.3.1.220 0.0164
-
malonyl-CoA pH 7.0, 30°C Garcinia mangostana

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.151 44000
-
2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation Garcinia mangostana
2.3.1.151 45618
-
2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation Garcinia mangostana
2.3.1.151 88000
-
His-tagged enzyme, gel filtration Garcinia mangostana
2.3.1.220 42700
-
xx * 42700, about, sequence calculation Garcinia mangostana

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.220 3 malonyl-CoA + benzoyl-CoA Garcinia mangostana
-
4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.151 Garcinia mangostana L7NCQ3
-
-
2.3.1.220 Garcinia mangostana L7NCQ3
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.151 recombinant C-terminally His-tagged BPS from Escherichia coli Garcinia mangostana

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.151 pericarp expression of GmBPS in fruit pericarp from an early stage Garcinia mangostana
-
2.3.1.220 fruit
-
Garcinia mangostana
-
2.3.1.220 pericarp
-
Garcinia mangostana
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.151 2 malonyl-CoA + 4-coumaroyl-CoA
-
Garcinia mangostana 3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one + 2 CO2
-
?
2.3.1.151 3 malonyl-CoA + acetyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
-
?
2.3.1.151 3 malonyl-CoA + benzoyl-CoA
-
Garcinia mangostana 4 CoA + 2,4,6-trihydroxybenzophenone + 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one + 4-hydroxy-6-phenyl-2H-pyran-2-one + 3 CO2 the recombinant enzyme produces 2,4,6-trihydroxybenzophenone as the predominant product with benzoyl CoA as substrate but also lactones of tetraketide and triketide type ?
2.3.1.151 3 malonyl-CoA + cinnamoyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 3 CO2
-
?
2.3.1.151 3 malonyl-CoA + hexanoyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-6-pentyl-2H-pyran-2-one + 5-hexanoyl-4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
-
?
2.3.1.151 3 malonyl-CoA + phenylacetyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-6-(2-oxo-3-phenylpropyl)-2H-pyran-2-one + 6-benzyl-4-hydroxy-2H-pyran-2-one + 2-phenyl-1-(2,4,6-trihydroxyphenyl)ethanone + 3 CO2
-
?
2.3.1.151 3 malonyl-CoA + salicyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-2H-chromen-2-one + 3 CO2
-
?
2.3.1.151 4 malonyl-CoA
-
Garcinia mangostana 4 CoA + 4-hydroxy-6-methyl-2H-pyran-2-one + 3 CO2
-
?
2.3.1.151 additional information with acetyl CoA or malonyl CoA as a starter substrate, the enzyme only produces a triacetic lactone of triketide lactone type, with phenylacetyl-Coa also lactones of tetraketide and triketide type, and with hexanoyl-CoA phloroglucinol and triketide type lactones, substrate specificity, overview Garcinia mangostana ?
-
?
2.3.1.220 3 malonyl-CoA + benzoyl-CoA
-
Garcinia mangostana 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
?
2.3.1.220 3 malonyl-CoA + benzoyl-CoA a minor amount of tetraketide lactone and triketide lactone are also obtained Garcinia mangostana 4 CoA + 2,4,6-trihydroxybenzophenone + 3 CO2
-
?
2.3.1.220 additional information the recombinant enzyme produces 2,4,6-trihydroxybenzophenone as the predominant product with benzoyl CoA as substrate. It also accepts other substrates, such as other plant PKSs, and used 1-3 molecules of malonyl CoA to form various phloroglucinol-type and polyketide lactone-type compounds Garcinia mangostana ?
-
?

Subunits

EC Number Subunits Comment Organism
2.3.1.151 dimer 2 * 44000, His-tagged enzyme, SDS-PAGE; 2 * 45618, His-tagged enzyme, sequence calculation Garcinia mangostana
2.3.1.220 ? xx * 42700, about, sequence calculation Garcinia mangostana

Synonyms

EC Number Synonyms Comment Organism
2.3.1.151 BPS
-
Garcinia mangostana
2.3.1.220 benzophenone synthase
-
Garcinia mangostana
2.3.1.220 BPS
-
Garcinia mangostana

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.151 30
-
recombinant His-tagged BPS Garcinia mangostana
2.3.1.220 30
-
-
Garcinia mangostana

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.151 0.049
-
benzoyl-CoA pH 7.0, 30°C, recombinant His-tagged BPS Garcinia mangostana
2.3.1.151 0.058
-
malonyl-CoA pH 7.0, 30°C, recombinant His-tagged BPS Garcinia mangostana
2.3.1.220 0.0495
-
benzoyl-CoA pH 7.0, 30°C Garcinia mangostana
2.3.1.220 0.0582
-
malonyl-CoA pH 7.0, 30°C Garcinia mangostana

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.151 6.5 7 recombinant His-tagged BPS Garcinia mangostana
2.3.1.220 6.5 7
-
Garcinia mangostana

pI Value

EC Number Organism Comment pI Value Maximum pI Value
2.3.1.151 Garcinia mangostana sequence calculation
-
5.97
2.3.1.220 Garcinia mangostana sequence calculation
-
5.97

General Information

EC Number General Information Comment Organism
2.3.1.151 evolution Garcinia mangostana BPS is an enzyme in the family of type III polyketide synthases and shows an amino acid sequence identity of 77-78% with other plant BPSs belonging to the same family (Clusiaceae). The three BPSs from the xanthone-rich Clusiaceae plants, Garcinia mangostana, Hypericum androsaemum, and Hypericum perforatum, suggest a close evolutionary relationship among these enzymes Garcinia mangostana
2.3.1.151 additional information the catalytic triad is formed by Cys164, His303, and Asn336 Garcinia mangostana
2.3.1.220 evolution phylogenetic tree Garcinia mangostana
2.3.1.220 metabolism the enzyme catalyzes the formation of an intermediate, 2,4,6-trihydroxybenzophenone, in the biosynthetic pathway of alpha-mangostin Garcinia mangostana
2.3.1.220 additional information the catalytic triad is formed by Cys164, His303, and Asn336 Garcinia mangostana

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.3.1.220 3.55
-
malonyl-CoA pH 7.0, 30°C Garcinia mangostana
2.3.1.220 5.14
-
benzoyl-CoA pH 7.0, 30°C Garcinia mangostana