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2-hydroxyisoflavanone synthase (2HI synthase) (EC 1.14.13.136) (CYP Ge-8) (Cytochrome P450 93C2) (Isoflavonoid synthase)

 C93C2_GLYEC             Reviewed;         523 AA.
Q9SXS3;
31-OCT-2012, integrated into UniProtKB/Swiss-Prot.
01-MAY-2000, sequence version 1.
12-SEP-2018, entry version 74.
RecName: Full=2-hydroxyisoflavanone synthase;
Short=2HI synthase;
EC=1.14.14.87 {ECO:0000269|PubMed:10557230, ECO:0000269|PubMed:12207646, ECO:0000269|PubMed:15809082};
AltName: Full=CYP Ge-8;
AltName: Full=Cytochrome P450 93C2;
AltName: Full=Isoflavonoid synthase;
Name=CYP93C2; Synonyms=IFS;
Glycyrrhiza echinata (Licorice).
Eukaryota; Viridiplantae; Streptophyta; Embryophyta; Tracheophyta;
Spermatophyta; Magnoliophyta; eudicotyledons; Gunneridae;
Pentapetalae; rosids; fabids; Fabales; Fabaceae; Papilionoideae;
50 kb inversion clade; NPAAA clade; Hologalegina; IRL clade; Galegeae;
Glycyrrhiza.
NCBI_TaxID=46348;
[1]
NUCLEOTIDE SEQUENCE [MRNA], FUNCTION, CATALYTIC ACTIVITY, INDUCTION BY
ELICITORS, AND SUBCELLULAR LOCATION.
PubMed=10557230; DOI=10.1104/pp.121.3.821;
Akashi T., Aoki T., Ayabe S.;
"Cloning and functional expression of a cytochrome P450 cDNA encoding
2-hydroxyisoflavanone synthase involved in biosynthesis of the
isoflavonoid skeleton in licorice.";
Plant Physiol. 121:821-828(1999).
[2]
FUNCTION, CATALYTIC ACTIVITY, MUTAGENESIS OF ARG-104; GLN-106;
VAL-119; SER-305; SER-310 AND LYS-375, BIOPHYSICOCHEMICAL PROPERTIES,
AND 3D-STRUCTURE MODELING.
PubMed=12207646; DOI=10.1046/j.1365-313X.2002.01378.x;
Sawada Y., Kinoshita K., Akashi T., Aoki T., Ayabe S.;
"Key amino acid residues required for aryl migration catalysed by the
cytochrome P450 2-hydroxyisoflavanone synthase.";
Plant J. 31:555-564(2002).
[3]
FUNCTION, CATALYTIC ACTIVITY, AND MUTAGENESIS OF SER-310; LEU-371 AND
LYS-375.
PubMed=15809082; DOI=10.1016/j.bbrc.2005.03.053;
Sawada Y., Ayabe S.;
"Multiple mutagenesis of P450 isoflavonoid synthase reveals a key
active-site residue.";
Biochem. Biophys. Res. Commun. 330:907-913(2005).
-!- FUNCTION: 2-hydroxyisoflavanone synthase, which catalyzes the
hydroxylation associated with 1,2-aryl migration of flavanones.
Converts liquiritigenin and naringenin into highly unstable
precursors of the isoflavones daidzein and genistein. Acts only on
substrates with (2S)-chirality. {ECO:0000269|PubMed:10557230,
ECO:0000269|PubMed:12207646, ECO:0000269|PubMed:15809082}.
-!- CATALYTIC ACTIVITY: Liquiritigenin + O(2) + [reduced NADPH--
hemoprotein reductase] = 2,4',7-trihydroxyisoflavanone + H(2)O +
[oxidized NADPH--hemoprotein reductase].
{ECO:0000269|PubMed:10557230, ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
-!- CATALYTIC ACTIVITY: (2S)-naringenin + O(2) + [reduced NADPH--
hemoprotein reductase] = 2,4',5,7-tetrahydroxyisoflavanone + H(2)O
+ [oxidized NADPH--hemoprotein reductase].
{ECO:0000269|PubMed:10557230, ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
-!- COFACTOR:
Name=heme; Xref=ChEBI:CHEBI:30413; Evidence={ECO:0000250};
-!- BIOPHYSICOCHEMICAL PROPERTIES:
Kinetic parameters:
KM=8 uM for liquiritigenin {ECO:0000269|PubMed:12207646};
pH dependence:
Optimum pH is 7.5. {ECO:0000269|PubMed:12207646};
-!- SUBCELLULAR LOCATION: Microsome membrane {ECO:0000305}; Single-
pass membrane protein {ECO:0000305}.
-!- INDUCTION: Up-regulated upon elicitation.
{ECO:0000269|PubMed:10557230}.
-!- MISCELLANEOUS: Lys-375 is essential for the intramolecular aryl
migration of a flavanone molecule to produce the isoflavonoid
skeleton (PubMed:12207646). Arg-104 and Leu-371 are essential for
the correct P450 conformation (PubMed:12207646, PubMed:15809082).
{ECO:0000305|PubMed:12207646, ECO:0000305|PubMed:15809082}.
-!- SIMILARITY: Belongs to the cytochrome P450 family. {ECO:0000305}.
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EMBL; AB023636; BAA76380.1; -; mRNA.
ProteinModelPortal; Q9SXS3; -.
SMR; Q9SXS3; -.
KEGG; ag:BAA76380; -.
KO; K13257; -.
GO; GO:0005783; C:endoplasmic reticulum; IEA:UniProtKB-KW.
GO; GO:0016021; C:integral component of membrane; IEA:UniProtKB-KW.
GO; GO:0043231; C:intracellular membrane-bounded organelle; IDA:UniProtKB.
GO; GO:0031090; C:organelle membrane; IEA:UniProtKB-SubCell.
GO; GO:0033770; F:2-hydroxyisoflavanone synthase activity; IDA:UniProtKB.
GO; GO:0020037; F:heme binding; IEA:InterPro.
GO; GO:0005506; F:iron ion binding; IEA:InterPro.
GO; GO:0009717; P:isoflavonoid biosynthetic process; IDA:UniProtKB.
Gene3D; 1.10.630.10; -; 1.
InterPro; IPR001128; Cyt_P450.
InterPro; IPR017972; Cyt_P450_CS.
InterPro; IPR002401; Cyt_P450_E_grp-I.
InterPro; IPR036396; Cyt_P450_sf.
Pfam; PF00067; p450; 1.
PRINTS; PR00463; EP450I.
PRINTS; PR00385; P450.
SUPFAM; SSF48264; SSF48264; 1.
PROSITE; PS00086; CYTOCHROME_P450; 1.
1: Evidence at protein level;
Endoplasmic reticulum; Heme; Iron; Membrane; Metal-binding; Microsome;
Monooxygenase; NADP; Oxidoreductase; Transmembrane;
Transmembrane helix.
CHAIN 1 523 2-hydroxyisoflavanone synthase.
/FTId=PRO_0000419822.
TRANSMEM 2 22 Helical. {ECO:0000255}.
METAL 450 450 Iron (heme axial ligand). {ECO:0000250}.
MUTAGEN 104 104 R->A: Total loss of catalytic activity.
{ECO:0000269|PubMed:12207646}.
MUTAGEN 106 106 Q->E: No effect on catalytic activity.
{ECO:0000269|PubMed:12207646}.
MUTAGEN 119 119 V->L: No effect on catalytic activity.
{ECO:0000269|PubMed:12207646}.
MUTAGEN 305 305 S->T: No effect on catalytic activity.
{ECO:0000269|PubMed:12207646}.
MUTAGEN 310 310 S->A,V: Decreased intramolecular 1,2-aryl
migration and increased production of 3-
hydroxyflavanone and flavone.
{ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
MUTAGEN 310 310 S->T: Decreased intramolecular 1,2-aryl
migration and increased production of 3-
hydroxyflavanone and flavone. 5% activity
and production of mainly 3-
hydroxyflavanone; when associated with T-
375. 0.1% activity and production of only
flavone; when associated with V-371 and
T-375. {ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
MUTAGEN 371 371 L->I: Production of mainly 3-
hydroxyflavanone; when associated with T-
375. {ECO:0000269|PubMed:15809082}.
MUTAGEN 371 371 L->V: Total loss of catalytic activity.
5% activity and production of mainly 3-
hydroxyflavanone; when associated with T-
375. 0.1% activity and production of only
flavone; when associated with T-310 and
T-375. {ECO:0000269|PubMed:15809082}.
MUTAGEN 375 375 K->A,R: Loss of intramolecular 1,2-aryl
migration and production of only 3-
hydroxyflavanone.
{ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
MUTAGEN 375 375 K->T: Loss of intramolecular 1,2-aryl
migration and production of only 3-
hydroxyflavanone. 5% activity and
production of mainly 3-hydroxyflavanone;
when associated with T-310; I-371 or V-
371. 0.1% activity and production of only
flavone; when associated with T-310 and
V-371. {ECO:0000269|PubMed:12207646,
ECO:0000269|PubMed:15809082}.
SEQUENCE 523 AA; 59429 MW; A0E7F1127847BAB2 CRC64;
MLVELAITLL VIALFIHLRP TLSAKSKSLR HLPNPPSPKP RLPFVGHLHL LDKPLLHYSL
IDLSKRYGPL YSLYFGSMPT VVASTPELFK LFLQTHEASS FNTRFQTSAI RRLTYDNSVA
MVPFGPYWKF IRKLIMNDLL NATTVNKLRP LRSQEIRKVL RVMAQSAESQ VPLNVTEELL
KWTNSTISRM MLGEAEEIRD IARDVLKIFG EYSLTDFIWP LKKLKVGQYE KRIDDIFNRF
DPVIERVIKK RQEIRKKRKE RNGEIEEGEQ SVVFLDTLLD FAEDETMEIK ITKEQIKGLV
VDFFSAGTDS TAVATDWALS ELINNPRVFQ KAREEIDAVV GKDRLVDEAD VQNLPYIRSI
VKETFRMHPP LPVVKRKCVQ ECEVDGYVIP EGALILFNVW AVGRDPKYWD RPTEFRPERF
LENVGEGDQA VDLRGQHFQL LPFGSGRRMC PGVNLATAGM ATLLASVIQC FDLSVVGPQG
KILKGNDAKV SMEERAGLTV PRAHNLICVP VARSSAVPKL FSS


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