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Information on EC 1.14.20.5 - flavone synthase I and Organism(s) Petroselinum crispum and UniProt Accession Q7XZQ8
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1.14.20.5 flavone synthase IIUBMB Comments
The enzyme, which has been found in rice and in members of the Apiaceae (a plant family), is a member of the 2-oxoglutarate-dependent dioxygenases, and requires ascorbate and Fe2+ for full activity.
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Word Map
- 1.14.20.5
- apigenin
- flavonols
- naringenin
- chalcone
- luteolin
-
2-oxoglutarate-dependent
- apiaceae
-
3beta-hydroxylase
- parsley
- eriodictyol
- 2s-naringenin
- fnsiis
- crispum
- anthocyanidins
-
c-glycosides
-
petroselinum
- 7,4'-dihydroxyflavone
-
2s-flavanones
- dihydroquercetin
-
2-hydroxyflavanone
- genkwanin
- synthesis
- biotechnology
The taxonomic range for the selected organisms is: Petroselinum crispum
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
flavone synthase, fns i, flavone synthase i, osfns, pfns-1, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
SYSTEMATIC NAME
IUBMB Comments
flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
The enzyme, which has been found in rice and in members of the Apiaceae (a plant family), is a member of the 2-oxoglutarate-dependent dioxygenases, and requires ascorbate and Fe2+ for full activity.
CAS REGISTRY NUMBER
COMMENTARY
138263-98-6
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-pinocembrin + 2-oxoglutarate + O2
chrysin + succinate + CO2 + H2O
-
-
-
?
cis-dihydrokaempferol + 2-oxoglutarate + O2
kaempferol + succinate + CO2 + H2O
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
luteolin + succinate + CO2 + H2O
-
-
-
?
naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
?
pinocembrin + 2-oxoglutarate + O2
chrysin + succinate + CO2 + H2O
-
-
-
?
(2S)-eriodictyol + 2-oxoglutarate + O2
luteolin + succinate + CO2 + H2O
-
-
-
-
ir
(2S)-naringenin + 2-oxoglutarate + O2
apigenin + succinate + H2O + CO2
-
-
-
-
?
eriodictyol + 2-oxoglutarate + O2
?
-
24% of the activity with naringenin
-
-
?
hesperetin + 2-oxoglutarate + O2
3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-chromen-4-one + succinate + CO2 + H2O
-
26% of the activity with naringenin
-
-
?
homoeriodictyol + 2-oxoglutarate + O2
5,7,4'-trihydroxy-3'-methoxyflavone + succinate + CO2 + H2O
-
97% of the activity with naringenin
-
-
?
naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
-
?
pinocembrin + 2-oxoglutarate + O2
chrysin + succinate + CO2 + H2O
-
24% of the activity with naringenin
-
-
?
additional information
?
-
-
no activity with 5,7-dihydroxy-3',4',5'-O-trimethyl-flavanone,7-O-methyl-pinocembrin, 5-O-methyl-pinocembrin, 5,7-O-dimethyl-pinocembrin
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
-
?
(2S)-naringenin + 2-oxoglutarate + O2
apigenin + succinate + CO2 + H2O
-
-
-
-
ir
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Fe2+
-
required for full activity, cannot be replaced by Mn2+, Co2+ or Ni2+
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ascorbate
-
required for full activity, can not be replaced as a reductant by 2-mercaptoethanol or dithiothreitol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
induced by continous irradiation with ultraviolet/blue light for 20 h
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). FNSI_PETCR
365
0
41024
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
transgenic seedlings of Arabidopsis thaliana accumulate substantial amounts of apigenin, and the apigenin level correlates with the abundance of enzyme mRNA
additional information
-
transgenic seedlings of Arabidopsis thaliana accumulate substantial amounts of apigenin, and the apigenin level correlates with the abundance of enzyme mRNA
additional information
-
domain swapping experiments joining the N-terminus of flavanone 3beta-hydroxylase with the C-terminus of flavone synthase I and vice versa. Conversion of seven active site residues of flavanone 3beta-hydroxylase into the corresponding amino acids of flavone synthase I causes a nearly complete change in enzyme activity from flavanone 3beta-hydroxylase to flavone synthase I
additional information
-
use of enzyme for construction of a system for producing unnatural flavonoids and stilbenes in Escherichia coli by expression of the respective genes on three plasmids. Incubation of the recombinant Escherichia coli with exogenously supplied carboxylic acids leads to production of 87 different polyketides, including 36 unnatural flavonoids and stilbenes
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
use of enzyme for construction of a system for producing unnatural flavonoids and stilbenes in Escherichia coli by expression of the respective genes on three plasmids. Incubation of the recombinant Escherichia coli with exogenously supplied carboxylic acids leads to production of 87 different polyketides, including 36 unnatural flavonoids and stilbenes
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Britsch, L.
Purification and characterization of flavone synthase I, a 2-oxoglutarate-dependent desaturase
Arch. Biochem. Biophys.
282
152-160
1990
Petroselinum crispum
Lukacin, R.; Matern, U.; Junghanns, K.T.; Heskamp, M.L.; Britsch, L.; Forkmann, G.; Martens, S.
Purification and antigenicity of flavone synthase I from irradiated parsley cells
Arch. Biochem. Biophys.
393
177-183
2001
Petroselinum crispum
Martens, S.; Forkmann, G.; Britsch, L.; Wellmann, F.; Matern, U.; Lukacin, R.
Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley
FEBS Lett.
544
93-98
2003
Petroselinum crispum (Q7XZQ8), Petroselinum crispum
Martens, S.; Forkmann, G.; Matern, U.; Lukacin, R.
Cloning of parsley flavone synthase I
Phytochemistry
58
43-46
2001
Petroselinum crispum
Schroeder, G.; Wehinger, E.; Lukacin, R.; Wellmann, F.; Seefelder, W.; Schwab, W.; Schroeder, J.
Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases
Phytochemistry
65
1085-1094
2004
Petroselinum crispum
Leonard, E.; Yan, Y.; Lim, K.H.; Koffas, M.A.
Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae
Appl. Environ. Microbiol.
71
8241-8248
2005
Petroselinum crispum (Q7XZQ8)
Leonard, E.; Chemler, J.; Lim, K.H.; Koffas, M.A.
Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli
Appl. Microbiol. Biotechnol.
70
85-91
2006
Petroselinum crispum
Miyahisa, I.; Funa, N.; Ohnishi, Y.; Martens, S.; Moriguchi, T.; Horinouchi, S.
Combinatorial biosynthesis of flavones and flavonols in Escherichia coli
Appl. Microbiol. Biotechnol.
71
53-58
2006
Petroselinum crispum (Q7XZQ8), Petroselinum crispum
Martens, S.; Mithoefer, A.
Flavones and flavone synthases
Phytochemistry
66
2399-2407
2005
Petroselinum crispum
Katsuyama, Y.; Funa, N.; Miyahisa, I.; Horinouchi, S.
Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli
Chem. Biol.
14
613-621
2007
Petroselinum crispum
Yun, C.S.; Yamamoto, T.; Nozawa, A.; Tozawa, Y.
Expression of parsley flavone synthase I establishes the flavone biosynthetic pathway in Arabidopsis thaliana
Biosci. Biotechnol. Biochem.
72
968-973
2008
Petroselinum crispum (Q7XZQ8), Petroselinum crispum
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