1.14.14.162: flavanone 2-hydroxylase
This is an abbreviated version!
For detailed information about flavanone 2-hydroxylase, go to the full flat file.
Word Map on EC 1.14.14.162
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1.14.14.162
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flavone
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flavanones
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flavonoid
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c-glycosides
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naringenin
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2-hydroxyflavanone
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sativa
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apigenin
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c-glycosylation
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eriodictyol
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2s-flavanone
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luteolin
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tricin
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grasses
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echinata
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glycyrrhiza
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b-ring
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today
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c-glucosyltransferase
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licorice
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chrysoeriol
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7,4'-dihydroxyflavone
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5'-hydroxylase
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o-glycosylate
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synthesis
- 1.14.14.162
- flavone
- flavanones
- flavonoid
-
c-glycosides
- naringenin
- 2-hydroxyflavanone
- sativa
- apigenin
-
c-glycosylation
- eriodictyol
-
2s-flavanone
- luteolin
- tricin
- grasses
- echinata
- glycyrrhiza
-
b-ring
-
today
-
c-glucosyltransferase
- licorice
- chrysoeriol
- 7,4'-dihydroxyflavone
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5'-hydroxylase
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o-glycosylate
- synthesis
Reaction
Synonyms
(2S)-flavanone 2-hydroxylase, CYP93G2, EC 1.14.13.87, EC 1.14.14.140, F2H, licodione synthase, liquiritigenin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (licodione-forming), LS, More, Os06g01250, OsF2H
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1.14.14.162 flavanone 2-hydroxylaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 1.14.14.162 - flavanone 2-hydroxylase
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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)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
luteolin + [oxidized NADPH-hemoprotein reductase] + H2O
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product is formed after acid treatment
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?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
hydroxylation of liquiritigenin at C-2 and formation of licodione as a result of non-enzymatic hemiacetal opening, selectivity towards (2S)-flavanone
-
-
?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
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requires NAD(P)H and O2 for activity, the reaction mechanism is likely to be 2-hydroxylation of the flavanone molecule to yield 2-hydroxyliquiritigenin and the subsequent hemiacetal opening to give licodione, introduces one atom of oxygen into the substrate, NADH serves as hydride donor less effectively than NADPH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
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?
(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2
licodione + [oxidized NADPH-hemoprotein reductase] + H2O
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requires NAD(P)H and O2 for activity, the reaction mechanism is likely to be 2-hydroxylation of the flavanone molecule to yield 2-hydroxyliquiritigenin and the subsequent hemiacetal opening to give licodione, introduces one atom of oxygen into the substrate, NADPH serves as hydride donor more effectively than NADH
i.e. 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione
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?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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the product is further converted into apigenin when treated with acid
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?
(2S)-naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
selectivity towards (2S)-flavanone
the product is further converted into apigenin when treated with HCl
-
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
naringenin + [reduced NADPH-hemoprotein reductase] + O2
2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
additional information
?
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involved in flavonoid biosynthesis, may play a role symbiotic plant-microbe interactions
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-
?
