Information on EC 2.3.1.156 - phloroisovalerophenone synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.3.1.156
-
RECOMMENDED NAME
GeneOntology No.
phloroisovalerophenone synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cohumulone biosynthesis
-
-
humulone biosynthesis
-
-
hyperforin and adhyperforin biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
isovaleryl-CoA:malonyl-CoA acyltransferase
Closely related to EC 2.3.1.74, naringenin-chalcone synthase. The product, 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one, is phloroisovalerophenone. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter (alpha) acids in hops (Humulus lupulus).
CAS REGISTRY NUMBER
COMMENTARY hide
214265-40-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
suppression of chalcone synthase activity in both transient and stable chalcone synthase-silenced fruit results in a substantial decrease of acylphloroglucinol glucosides and anthocyanins and enhanced levels of volatiles derived from branched-chain amino acids
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
show the reaction diagram
isovaleryl-CoA + 3 malonyl-CoA
phloroisovalerophenone + 3 CO2 + 4 CoA
show the reaction diagram
-
isovaleryl-CoA is the preferred starter substrate of isoform CHS2-1
-
-
?
isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
isobutyryl-CoA + 3 malonyl-CoA
phloroisobutyrophenone + 3 CO2 + 4 CoA
show the reaction diagram
isovaleryl-CoA + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
show the reaction diagram
-
-
phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
?
additional information
?
-
O80400
the enzyme is responsible for the biosynthesis of the precursors of alpha-acid and beta-acid
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-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
isobutyryl-CoA
-
-
0.004
isovaleryl-CoA
-
-
0.033
malonyl-CoA
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
following the activity through the development of the glandular trichomes on the female flowers phlorisovalerophenone synthase shows the highest activity at 21-29 days
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high activity is found in male flowers
Manually annotated by BRENDA team
at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development; at early, mid, and late stages of development
Manually annotated by BRENDA team
specifically expressed in
Manually annotated by BRENDA team
additional information
no expression in leaf and stem
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
110000
-
native PAGE of purified VPS
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
homodimer, 2 * 45000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
low stability
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme
separation of benzophenone synthase, isobutyrophenone synthase, and chalcone synthase activities
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
characterization of the VPS cDNA clone
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expression in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
brewing
valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content; valerophenone synthase is a key gene in the bitter acid biosynthesis of hop, sequence analysis reveals nine single nucleotide polymorphisms in VPS,understanding variation in the genes of the bitter acid biosynthetic pathway is required to improve the content and quality of bitter acids in hop, real-time quantitative reverse-transcription polymerase chain reaction analysis shows a clear link between VPS expression and bitter acid content
nutrition
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cones of the hop plant used in the beer-brewing process
synthesis
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total enzymatic synthesis of acylphloroglucinol glucosides is achieved by co-incubation of recombinant dual functional chalcone/valerophenone synthase and UGT71K3 proteins with essential coenzyme A esters and UDP-glucose. Proteins UGT71K3a/b catalyze the glucosylation of diverse hydroxycoumarins, naphthols and flavonoids, enzymatically synthesized acylphloroglucinol aglycones and pelargonidin