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Chalcone--flavonone isomerase 1 (Chalcone isomerase 1) (EC 5.5.1.6)

 CFI1_MEDSA              Reviewed;         222 AA.
P28012;
01-AUG-1992, integrated into UniProtKB/Swiss-Prot.
01-AUG-1992, sequence version 1.
22-NOV-2017, entry version 88.
RecName: Full=Chalcone--flavonone isomerase 1;
Short=Chalcone isomerase 1;
EC=5.5.1.6;
Name=CHI1; Synonyms=CHI-1;
Medicago sativa (Alfalfa).
Eukaryota; Viridiplantae; Streptophyta; Embryophyta; Tracheophyta;
Spermatophyta; Magnoliophyta; eudicotyledons; Gunneridae;
Pentapetalae; rosids; fabids; Fabales; Fabaceae; Papilionoideae;
Trifolieae; Medicago.
NCBI_TaxID=3879;
[1]
NUCLEOTIDE SEQUENCE [MRNA].
STRAIN=cv. Iroquois;
PubMed=8193301; DOI=10.1007/BF00029858;
McKhann H.I., Hirsch A.M.;
"Isolation of chalcone synthase and chalcone isomerase cDNAs from
alfalfa (Medicago sativa L.): highest transcript levels occur in young
roots and root tips.";
Plant Mol. Biol. 24:767-777(1994).
[2]
ERRATUM.
McKhann H.I., Hirsch A.M.;
Plant Mol. Biol. 25:759-759(1994).
[3]
X-RAY CRYSTALLOGRAPHY (1.85 ANGSTROMS) IN COMPLEX WITH
(2S)-NARINGENIN, FUNCTION, BIOPHYSICOCHEMICAL PROPERTIES, AND
MUTAGENESIS OF TYR-106.
PubMed=10966651; DOI=10.1038/79025;
Jez J.M., Bowman M.E., Dixon R.A., Noel J.P.;
"Structure and mechanism of the evolutionarily unique plant enzyme
chalcone isomerase.";
Nat. Struct. Biol. 7:786-791(2000).
[4]
X-RAY CRYSTALLOGRAPHY (2.3 ANGSTROMS), FUNCTION, BIOPHYSICOCHEMICAL
PROPERTIES, AND MUTAGENESIS OF THR-48; TYR-106; ASN-113 AND THR-190.
PubMed=11955065; DOI=10.1021/bi0255266;
Jez J.M., Bowman M.E., Noel J.P.;
"Role of hydrogen bonds in the reaction mechanism of chalcone
isomerase.";
Biochemistry 41:5168-5176(2002).
[5]
X-RAY CRYSTALLOGRAPHY (2.1 ANGSTROMS), FUNCTION, AND
BIOPHYSICOCHEMICAL PROPERTIES.
PubMed=11698411; DOI=10.1074/jbc.M109224200;
Jez J.M., Noel J.P.;
"Reaction mechanism of chalcone isomerase. pH dependence, diffusion
control, and product binding differences.";
J. Biol. Chem. 277:1361-1369(2002).
-!- FUNCTION: Catalyzes the intramolecular cyclization of bicyclic
chalcones into tricyclic (S)-flavanones. Responsible for the
isomerization of 4,2',4',6'-tetrahydroxychalcone (also termed
chalcone) into naringenin. {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065}.
-!- CATALYTIC ACTIVITY: A chalcone = a flavanone.
-!- BIOPHYSICOCHEMICAL PROPERTIES:
Kinetic parameters:
KM=8.4 uM for 4,2',4'-trihydroxychalcone (at pH 7.5 and 25
degrees Celsius) {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
KM=15.7 uM for 6'-deoxychalcone (at pH 7.5 and 25 degrees
Celsius) {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
KM=22.7 uM for 2',4'-dihydroxychalcone (at pH 7.5 and 25 degrees
Celsius) {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
KM=42.5 uM for 4,2'-dihydroxychalcone (at pH 7.5 and 25 degrees
Celsius) {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
KM=112 uM for 4,2',4',6'-tetrahydroxychalcone (at pH 7.5 and 25
degrees Celsius) {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
pH dependence:
Optimum pH is 7-8.5 with 4,2',4'-trihydroxychalcone as
substrate, at 25 degrees Celsius. {ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11698411, ECO:0000269|PubMed:11955065};
-!- PATHWAY: Secondary metabolite biosynthesis; flavonoid
biosynthesis.
-!- DEVELOPMENTAL STAGE: Highest expression in young root tips.
-!- MISCELLANEOUS: Part of the biosynthetic pathway for all classes of
flavonoids, a large class of secondary plant metabolites, many of
which are brightly colored.
-!- SIMILARITY: Belongs to the chalcone isomerase family.
{ECO:0000305}.
-----------------------------------------------------------------------
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EMBL; M91079; AAB41524.1; -; mRNA.
PIR; S44371; S44371.
PDB; 1EYP; X-ray; 2.50 A; A/B=1-222.
PDB; 1EYQ; X-ray; 1.85 A; A/B=1-222.
PDB; 1FM7; X-ray; 2.30 A; A/B=1-222.
PDB; 1FM8; X-ray; 2.30 A; A/B=1-222.
PDB; 1JEP; X-ray; 2.10 A; A/B=1-222.
PDB; 1JX0; X-ray; 2.85 A; A/B=1-222.
PDB; 1JX1; X-ray; 2.30 A; A/B/C/D/E/F=1-222.
PDBsum; 1EYP; -.
PDBsum; 1EYQ; -.
PDBsum; 1FM7; -.
PDBsum; 1FM8; -.
PDBsum; 1JEP; -.
PDBsum; 1JX0; -.
PDBsum; 1JX1; -.
ProteinModelPortal; P28012; -.
SMR; P28012; -.
PRIDE; P28012; -.
BioCyc; MetaCyc:MONOMER-18291; -.
BRENDA; 5.5.1.6; 3078.
SABIO-RK; P28012; -.
UniPathway; UPA00154; -.
EvolutionaryTrace; P28012; -.
GO; GO:0045430; F:chalcone isomerase activity; IEA:UniProtKB-EC.
GO; GO:0009813; P:flavonoid biosynthetic process; IEA:UniProtKB-UniPathway.
Gene3D; 1.10.890.20; -; 1.
Gene3D; 3.50.70.10; -; 1.
InterPro; IPR016087; Chalcone_isomerase.
InterPro; IPR016088; Chalcone_isomerase_3-sand.
InterPro; IPR016089; Chalcone_isomerase_bundle_sf.
InterPro; IPR036298; Chalcone_isomerase_sf.
Pfam; PF02431; Chalcone; 1.
SUPFAM; SSF54626; SSF54626; 1.
1: Evidence at protein level;
3D-structure; Flavonoid biosynthesis; Isomerase.
CHAIN 1 222 Chalcone--flavonone isomerase 1.
/FTId=PRO_0000166434.
BINDING 48 48 Substrate. {ECO:0000250}.
BINDING 113 113 Substrate. {ECO:0000250}.
BINDING 190 190 Substrate. {ECO:0000250}.
SITE 106 106 Important for catalytic activity.
MUTAGEN 48 48 T->A: Strongly reduced reaction rate.
{ECO:0000269|PubMed:11955065}.
MUTAGEN 48 48 T->S: Reduced reaction rate.
{ECO:0000269|PubMed:11955065}.
MUTAGEN 106 106 Y->F: Strongly reduced reaction rate.
{ECO:0000269|PubMed:10966651,
ECO:0000269|PubMed:11955065}.
MUTAGEN 113 113 N->A: Reduced reaction rate.
{ECO:0000269|PubMed:11955065}.
MUTAGEN 190 190 T->A: Reduced reaction rate.
{ECO:0000269|PubMed:11955065}.
STRAND 8 10 {ECO:0000244|PDB:1EYQ}.
STRAND 13 15 {ECO:0000244|PDB:1EYQ}.
STRAND 17 20 {ECO:0000244|PDB:1EYQ}.
TURN 22 24 {ECO:0000244|PDB:1EYQ}.
STRAND 27 40 {ECO:0000244|PDB:1EYQ}.
STRAND 43 55 {ECO:0000244|PDB:1EYQ}.
HELIX 58 66 {ECO:0000244|PDB:1EYQ}.
HELIX 71 75 {ECO:0000244|PDB:1EYQ}.
HELIX 78 86 {ECO:0000244|PDB:1EYQ}.
STRAND 87 89 {ECO:0000244|PDB:1FM8}.
STRAND 91 99 {ECO:0000244|PDB:1EYQ}.
HELIX 103 120 {ECO:0000244|PDB:1EYQ}.
HELIX 126 139 {ECO:0000244|PDB:1EYQ}.
STRAND 142 144 {ECO:0000244|PDB:1JX1}.
STRAND 149 155 {ECO:0000244|PDB:1EYQ}.
TURN 156 158 {ECO:0000244|PDB:1EYQ}.
STRAND 159 169 {ECO:0000244|PDB:1EYQ}.
STRAND 175 179 {ECO:0000244|PDB:1EYQ}.
HELIX 181 192 {ECO:0000244|PDB:1EYQ}.
HELIX 200 214 {ECO:0000244|PDB:1EYQ}.
SEQUENCE 222 AA; 23826 MW; 7767A72084AB4800 CRC64;
MAASITAITV ENLEYPAVVT SPVTGKSYFL GGAGERGLTI EGNFIKFTAI GVYLEDIAVA
SLAAKWKGKS SEELLETLDF YRDIISGPFE KLIRGSKIRE LSGPEYSRKV MENCVAHLKS
VGTYGDAEAE AMQKFAEAFK PVNFPPGASV FYRQSPDGIL GLSFSPDTSI PEKEAALIEN
KAVSSAVLET MIGEHAVSPD LKRCLAARLP ALLNEGAFKI GN


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