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Information on EC 2.3.1.156 - phloroisovalerophenone synthase and Organism(s) Humulus lupulus and UniProt Accession O80400

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EC Tree
IUBMB Comments
Closely related to EC 2.3.1.74, naringenin-chalcone synthase. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter acids in hops (Humulus lupulus) and glucosides in strawberry (Fragaria X ananassa). It is also able to generate naringenin chalcone from 4-coumaroyl-CoA.
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This record set is specific for:
Humulus lupulus
UNIPROT: O80400
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Word Map
The taxonomic range for the selected organisms is: Humulus lupulus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
valerophenone synthase, phlorisovalerophenone synthase, chs2-1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
valerophenone synthase
-
3-methyl-1-(trihydroxyphenyl)butan-1-one synthase
-
-
-
-
valerophenone synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone
show the reaction diagram
Closely related to EC 2.3.1.74, chalcone synthase. The product, 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one, is chloroisovalerophenone. 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
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
SYSTEMATIC NAME
IUBMB Comments
isovaleryl-CoA:malonyl-CoA acyltransferase
Closely related to EC 2.3.1.74, naringenin-chalcone synthase. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter acids in hops (Humulus lupulus) and glucosides in strawberry (Fragaria X ananassa). It is also able to generate naringenin chalcone from 4-coumaroyl-CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
214265-40-4
-
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 + malonyl-CoA
phloroisovalerophenone + CO2 + CoA
show the reaction diagram
additional information
?
-
the enzyme is responsible for the biosynthesis of the precursors of alpha-acid and beta-acid
-
-
?
NATURAL SUBSTRATE
NATURAL 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
-
-
phloroglucinol derivative, intermediates in the biosynthesis of the hop bitter alpha- and beta-acids
?
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
?
-
the enzyme is responsible for the biosynthesis of the precursors of alpha-acid and beta-acid
-
-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
isobutyryl-CoA
-
-
0.004
isovaleryl-CoA
-
-
0.033
malonyl-CoA
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400
at early, mid, and late stages of development
Manually annotated by BRENDA team
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400
at early, mid, and late stages of development
Manually annotated by BRENDA team
specifically expressed in
Manually annotated by BRENDA team
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400
at early, mid, and late stages of development
Manually annotated by BRENDA team
additional information
no expression in leaf and stem
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
VPS_HUMLU
394
0
43080
Swiss-Prot
other Location (Reliability: 4)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
110000
-
native PAGE of purified VPS
45000
-
homodimer, 2 * 45000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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homodimer, 2 * 45000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
low stability
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
characterization of the VPS cDNA clone
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
brewing
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400
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
brewing
B3GEA8, B3GEA9, B3GEB0, B3GEB1, B3GEB2, B3GEB3, B3GEB4, B3GEB5, B3GEB6, O80400
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zuurbier, K.W.M.; Leser, J.; Berger, T.; Hofte, A.J.P.; Schroder, G.; Verpoorte, R.; Schroder, J.
4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates
Phytochemistry
49
1945-1951
1998
Humulus lupulus
Manually annotated by BRENDA team
Paniego, N.B.; Zuurbier, K.W.M.; Fung, S.Y.; Van der Heijden, R.; Scheffer, J.J.C.; Verpoorte, R.
Phlorisovalerophenone synthase, a novel polyketide synthase from hop (Humulus lupulus L.) cones
Eur. J. Biochem.
262
612-616
1999
Humulus lupulus
Manually annotated by BRENDA team
Okada, Y.; Ito, K.
Cloning and analysis of valerophenone synthase gene expressed specifically in lupulin gland of hop (Humulus lupulus L.)
Biosci. Biotechnol. Biochem.
65
150-155
2001
Humulus lupulus (O80400)
Manually annotated by BRENDA team
Castro, C.B.; Whittock, L.D.; Whittock, S.P.; Leggett, G.; Koutoulis, A.
DNA sequence and expression variation of hop (Humulus lupulus) valerophenone synthase (VPS), a key gene in bitter acid biosynthesis
Ann. Bot.
102
265-273
2008
Humulus lupulus (B3GEA8), Humulus lupulus (B3GEA9), Humulus lupulus (B3GEB0), Humulus lupulus (B3GEB1), Humulus lupulus (B3GEB2), Humulus lupulus (B3GEB3), Humulus lupulus (B3GEB4), Humulus lupulus (B3GEB5), Humulus lupulus (B3GEB6), Humulus lupulus (O80400)
Manually annotated by BRENDA team