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3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
acetoacetyl-CoA
monoacetylphloroglucinol + ?
acetoacetyl-CoA
phloroglucinol + 4-hydroxy-6-methyl-2H-pyran-2-one + CO2 + CoA
butyryl-CoA
phloroglucinol + 4-hydroxy-6-propyl-2H-pyran-2-one + CO2 + CoA
decanoyl-CoA
4-hydroxy-6-octyl-2H-pyran-2-one + 4-hydroxy-6-(2-oxoundecyl)-2H-pyran-2-one + 4-hydroxyl-6-(2',4',6'-trioxopentadecyl)-2-pyrone + CO2 + CoA
hexanoyl-CoA
4-hydroxy-6-pentyl-2H-pyran-2-one + 4-hydroxy-6-(2-oxoheptyl)-2H-pyran-2-one + CO2 + CoA
8% activity compared to malonyl-CoA
-
-
?
lauroyl-CoA
6-decyl-4-hydroxy-2H-pyran-2-one + 4-hydroxy-6-(2-oxotridecyl)-2H-pyran-2-one + CO2 + CoA
7.6% activity compared to malonyl-CoA
-
-
?
octanoyl-CoA
6-heptyl-4-hydroxy-2H-pyran-2-one + 4-hydroxy-6-(2-oxononyl)-2H-pyran-2-one + 4-hydroxyl-6-(2',4',6'-trioxotridecyl)-2-pyrone + 4-hydroxyl-6-(2',4',6',8'-tetraoxopentadecyl)-2-pyrone + CO2 + CoA
7% activity compared to malonyl-CoA
-
-
?
phenylacetyl-CoA
6-(cyclohepta-1,3,6-trien-1-yl)-4-hydroxy-2H-pyran-2-one + 6-[2-(cyclohepta-1,3,6-trien-1-yl)-2-oxoethyl]-4-hydroxy-2H-pyran-2-one + CO2 + CoA
3.3% activity compared to malonyl-CoA
-
-
?
additional information
?
-
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
phloroglucinol is 1,3,5-trihydroxylbenzene
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
preferred substrate
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
phloroglucinol is 1,3,5-trihydroxylbenzene
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
preferred substrate
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
acetoacetyl-CoA
monoacetylphloroglucinol + ?
-
-
-
-
?
acetoacetyl-CoA
monoacetylphloroglucinol + ?
-
-
-
-
?
acetoacetyl-CoA
phloroglucinol + 4-hydroxy-6-methyl-2H-pyran-2-one + CO2 + CoA
1.6% activity compared to malonyl-CoA
-
-
?
acetoacetyl-CoA
phloroglucinol + 4-hydroxy-6-methyl-2H-pyran-2-one + CO2 + CoA
1.6% activity compared to malonyl-CoA
-
-
?
butyryl-CoA
phloroglucinol + 4-hydroxy-6-propyl-2H-pyran-2-one + CO2 + CoA
0.2% activity compared to malonyl-CoA
-
-
?
butyryl-CoA
phloroglucinol + 4-hydroxy-6-propyl-2H-pyran-2-one + CO2 + CoA
0.2% activity compared to malonyl-CoA
-
-
?
decanoyl-CoA
4-hydroxy-6-octyl-2H-pyran-2-one + 4-hydroxy-6-(2-oxoundecyl)-2H-pyran-2-one + 4-hydroxyl-6-(2',4',6'-trioxopentadecyl)-2-pyrone + CO2 + CoA
18% activity compared to malonyl-CoA
-
-
?
decanoyl-CoA
4-hydroxy-6-octyl-2H-pyran-2-one + 4-hydroxy-6-(2-oxoundecyl)-2H-pyran-2-one + 4-hydroxyl-6-(2',4',6'-trioxopentadecyl)-2-pyrone + CO2 + CoA
18% activity compared to malonyl-CoA
-
-
?
additional information
?
-
the enzyme shows barely detectable activity toward acetyl-CoA, isobutyryl-CoA, benzoyl-CoA, and crotonyl-CoA. No activity with myristoyl-CoA and palmitoyl-CoA
-
-
?
additional information
?
-
acetate is successfully transformed into phloroglucinol by the combined activity of recombinant acetyl-CoA carboxylase (ACC) from Acinetobacter calcoaceticus strain CGMCC 1.6186 and recombinant phloroglucinol synthase (PhlD) from Pseudomonas fluorescens strain Pf-5 in an in vitro system, synthetic pathway of phloroglucinol and in vitro synthesis of phloroglucinol from acetate, method optimization, overview
-
-
-
additional information
?
-
acetate is successfully transformed into phloroglucinol by the combined activity of recombinant acetyl-CoA carboxylase (ACC) from Acinetobacter calcoaceticus strain CGMCC 1.6186 and recombinant phloroglucinol synthase (PhlD) from Pseudomonas fluorescens strain Pf-5 in an in vitro system, synthetic pathway of phloroglucinol and in vitro synthesis of phloroglucinol from acetate, method optimization, overview
-
-
-
additional information
?
-
acetate is successfully transformed into phloroglucinol by the combined activity of recombinant acetyl-CoA carboxylase (ACC) from Acinetobacter calcoaceticus strain CGMCC 1.6186 and recombinant phloroglucinol synthase (PhlD) from Pseudomonas fluorescens strain Pf-5 in an in vitro system, synthetic pathway of phloroglucinol and in vitro synthesis of phloroglucinol from acetate, method optimization, overview
-
-
-
additional information
?
-
the enzyme shows barely detectable activity toward acetyl-CoA, isobutyryl-CoA, benzoyl-CoA, and crotonyl-CoA. No activity with myristoyl-CoA and palmitoyl-CoA
-
-
?
additional information
?
-
acetate is successfully transformed into phloroglucinol by the combined activity of recombinant acetyl-CoA carboxylase (ACC) from Acinetobacter calcoaceticus strain CGMCC 1.6186 and recombinant phloroglucinol synthase (PhlD) from Pseudomonas fluorescens strain Pf-5 in an in vitro system, synthetic pathway of phloroglucinol and in vitro synthesis of phloroglucinol from acetate, method optimization, overview
-
-
-
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3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
phloroglucinol is 1,3,5-trihydroxylbenzene
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
preferred substrate
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
phloroglucinol is 1,3,5-trihydroxylbenzene
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
preferred substrate
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
3 malonyl-CoA
phloroglucinol + 3 CO2 + 3 CoA
-
-
-
?
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A181S
-
the mutant shows 110% of wild type specific activity
A289R
the mutant shows 1.4fold improved catalytic efficiency compared to the wild type enzyme
A60L
the mutant still retains the wild type activity to react with lauroyl-CoA
A82T
-
the mutant shows wild type specific activity
H24L
the mutant shows reduced reactivity toward lauroyl-CoA and has lost the ability to produce phloroglucinol
H24V
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
K210L
the mutant shows 1.9fold improved catalytic efficiency compared to the wild type enzyme
K210L/Y256R
the mutant shows 0.9fold improved catalytic efficiency compared to the wild type enzyme
L136M/S243T
-
the mutant shows 90% of wild type specific activity
L54V
-
the mutant shows 110% of wild type specific activity
L54V/A82T
-
the mutant shows wild type specific activity
L59M
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
M21I
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
M21T/L54V/A82T
-
the mutant shows 90% of wild type specific activity
M21T/L54V/A82T/A181S
-
the mutant shows wild type specific activity
M21T/L54V/A82T/S96R/A181S
-
the mutant shows 110% of wild type specific activity
M21T/N27D/A82T/A181S
-
the mutant shows 90% of wild type specific activity
M21T/N27D/L54V/A82T/A181S/S243T
-
the mutant shows wild type specific activity
M21T/N27D/L54V/A82T/L136M/A181S/S243T
-
the mutant shows 110% of wild type specific activity
N27D
-
the mutant shows 90% of wild type specific activity
S96R
-
the mutant shows 80% of wild type specific activity
Y256R
the mutant shows 1.9fold improved catalytic efficiency compared to the wild type enzyme
Y256R/A289R
the mutant shows 0.8fold improved catalytic efficiency compared to the wild type enzyme
A181S
-
the mutant shows 110% of wild type specific activity
-
A289R
-
the mutant shows 1.4fold improved catalytic efficiency compared to the wild type enzyme
-
A82T
-
the mutant shows wild type specific activity
-
H24L
-
the mutant shows reduced reactivity toward lauroyl-CoA and has lost the ability to produce phloroglucinol
-
H24V
-
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
-
K210L
-
the mutant shows 1.9fold improved catalytic efficiency compared to the wild type enzyme
-
K210L/Y256R
-
the mutant shows 0.9fold improved catalytic efficiency compared to the wild type enzyme
-
L136M/S243T
-
the mutant shows 90% of wild type specific activity
-
L54V
-
the mutant shows 110% of wild type specific activity
-
L59M
-
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
-
M21I
-
the mutation significantly reduces the reactivity of the enzyme with lauroyl-CoA while still retaining its physiological activity to synthesize phloroglucinol
-
M21T
-
the mutant still retains the wild type activity to react with lauroyl-CoA
-
N27D
-
the mutant shows 90% of wild type specific activity
-
Y256R
-
the mutant shows 1.9fold improved catalytic efficiency compared to the wild type enzyme
-
Y256R/A289R
-
the mutant shows 0.8fold improved catalytic efficiency compared to the wild type enzyme
-
M21T
-
the mutant shows 90% of wild type specific activity
M21T
the mutant still retains the wild type activity to react with lauroyl-CoA
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Cao, Y.; Jiang, X.; Zhang, R.; Xian, M.
Improved phloroglucinol production by metabolically engineered Escherichia coli
Appl. Microbiol. Biotechnol.
91
1545-1552
2011
Pseudomonas fluorescens, Pseudomonas fluorescens Pf-5
brenda
Rao, G.; Lee, J.K.; Zhao, H.
Directed evolution of phloroglucinol synthase PhlD with increased stability for phloroglucinol production
Appl. Microbiol. Biotechnol.
97
5861-5867
2013
Pseudomonas fluorescens, Pseudomonas fluorescens Pf-5
brenda
Achkar, J.; Xian, M.; Zhao, H.; Frost, J.W.
Biosynthesis of phloroglucinol
J. Am. Chem. Soc.
127
5332-5333
2005
Pseudomonas fluorescens, Pseudomonas fluorescens Pf-5
brenda
Bangera, M.G.; Thomashow, L.S.
Identification and characterization of a gene cluster for synthesis of the polyketide antibiotic 2,4-diacetylphloroglucinol from Pseudomonas fluorescens Q2-87
J. Bacteriol.
181
3155-3163
1999
Pseudomonas fluorescens, Pseudomonas fluorescens Q2-87
brenda
Zha, W.; Rubin-Pitel, S.B.; Zhao, H.
Characterization of the substrate specificity of PhlD, a type III polyketide synthase from Pseudomonas fluorescens
J. Biol. Chem.
281
32036-32047
2006
Pseudomonas fluorescens (Q4K418), Pseudomonas fluorescens Pf-5 (Q4K418)
brenda
Zha, W.; Rubin-Pitel, S.B.; Zhao, H.
Exploiting genetic diversity by directed evolution: molecular breeding of type III polyketide synthases improves productivity
Mol. Biosyst.
4
246-248
2008
Pseudomonas fluorescens (Q4K418), Pseudomonas fluorescens Pf-5 (Q4K418)
brenda
Ramette, A.; Moenne-Loccoz, Y.; Defago, G.
Polymorphism of the polyketide synthase gene phID in biocontrol fluorescent pseudomonads producing 2,4-diacetylphloroglucinol and comparison of PhID with plant polyketide synthases
Mol. Plant Microbe Interact.
14
639-652
2001
Pseudomonas fluorescens (Q9REL4), Pseudomonas fluorescens (Q9REL5), Pseudomonas fluorescens (Q9REM4), Pseudomonas fluorescens (Q9REZ8), Pseudomonas fluorescens (Q9REZ9), Pseudomonas fluorescens Pf-5 (Q9REL4), Pseudomonas fluorescens UP61 (Q9REM4), Pseudomonas fluorescens Q8r1-96 (Q9REZ8), Pseudomonas fluorescens M1-96 (Q9REZ9), Pseudomonas fluorescens CHA0 (Q9REL5)
brenda
Zhang, R.; Liu, W.; Cao, Y.; Xu, X.; Xian, M.; Liu, H.
An in vitro synthetic biosystem based on acetate for production of phloroglucinol
BMC Biotechnol.
17
66
2017
Pseudomonas fluorescens (Q4K418), Pseudomonas fluorescens Pf-5 (Q4K418), Pseudomonas fluorescens ATCC BAA-477 (Q4K418), Pseudomonas fluorescens NRRL B-23932 (Q4K418)
brenda