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Information on EC 5.5.1.6 - chalcone isomerase and Organism(s) Medicago sativa and UniProt Accession P28012

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Medicago sativa
UNIPROT: P28012 not found.
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The taxonomic range for the selected organisms is: Medicago sativa
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
chalcone isomerase, chalcone-flavanone isomerase, chi-1, chil1, mpchi, slchi1, chil2, chi1a, chalcone isomerase-like protein, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Chalcone isomerase
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-
-
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Chalcone-flavanone isomerase
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-
-
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Isomerase, chalcone
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-
-
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TRANSPARENT TESTA 5 protein
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-
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
A chalcone = a flavanone
show the reaction diagram
rate limiting step is an intramolecular Michael addition of a 2’-oxyanion to the alpha,beta-double bond. Computational study shows that the active site conformation with larger catalytic power presents a positively charged lysine resiude much closer to the substrate than the second active site. Charge is transferred from the 2’-oxyanion to the beta-carbon atom
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
flavanone lyase (decyclizing)
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CAS REGISTRY NUMBER
COMMENTARY hide
9073-57-8
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2',4'-dihydroxychalcone
7-hydroxy-2-phenyl-chroman-4-one
show the reaction diagram
-
-
-
?
2',4-dihydroxychalcone
?
show the reaction diagram
-
-
?
4,2',4',6'-tetrahydrochalcone
?
show the reaction diagram
-
-
?
4,2',4'-trihydrochalcone
?
show the reaction diagram
-
-
?
4,2'-dihydrochalcone
?
show the reaction diagram
-
-
?
chalcone
(2S)-flavanone
show the reaction diagram
-
-
-
?
6'-deoxychalcone
(2S)-liquiritigenin
show the reaction diagram
-
-
-
-
?
6'-deoxychalcone
?
show the reaction diagram
6'-hydroxychalcone
(2S)-naringenin
show the reaction diagram
-
-
-
-
?
Chalcone
Flavanone
show the reaction diagram
-
-
-
-
?
additional information
?
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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
additional information
?
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0227
2',4'-dihydroxychalcone
pH 7.5, 25°C
0.112
4,2',4',6'-tetrahydrochalcone
pH 7.5, 25°C
0.0084
4,2',4'-trihydrochalcone
pH 7.5, 25°C
0.0425
4,2'-dihydrochalcone
pH 7.5, 25°C
0.02987
6'-Deoxychalcone
-
at pH 7.5 and 35°C
0.05365
6'-hydroxychalcone
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at pH 7.5 and 35°C
additional information
additional information
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calculated and experimentally-derived free-energy barriers for the Michael addition of the deprotonated forms of chalcone and 6'-deoxychalcone in aqueous solution and enzyme. Substrates may exist in at least two different conformational forms according to the relative disposition of the carbonyl group and the alpha,beta-double bond. Only the S-trans conformer, which is not the most stable one in aqueous solution, is able to proceed up to the reaction products
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
45300
2',4'-dihydroxychalcone
pH 7.5, 25°C
670800 - 671000
4,2',4',6'-tetrahydrochalcone
135000
4,2',4'-trihydrochalcone
pH 7.5, 25°C
5526 - 5530
4,2'-dihydrochalcone
7.06
6'-Deoxychalcone
-
at pH 7.5 and 35°C
103
6'-hydroxychalcone
-
at pH 7.5 and 35°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
236.7
6'-Deoxychalcone
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at pH 7.5 and 35°C
1916.7
6'-hydroxychalcone
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at pH 7.5 and 35°C
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
at pH 7.5 reactions of 4,2',4',6'-tetrahydrochalcone and 4,2',4'-trihydrochalcone and 2',4'-dihydroxychalcone are 90% diffusion controlled, whereas cyclization of 4,2'-dihydroxychalcone is limited by a chemical step that likely reflects the higher pKa of the 2'-hydroxyl group. At pH 6.0 the reactions with 4,2',4',6'-tetrahydrochalcone and 4,2',4'-trihydroxychalcone are 50% diffusion limited, whereas the reactions of 2',4'-dihydroxychalcone and 4,2'-dihydroxychalcone are limited by chemical steps
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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elicitor-treated
Manually annotated by BRENDA team
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very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
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very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
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high activity in tips and young roots. Low activity in root nodules elicited by wild-type strains of Rhizobium meliloti
Manually annotated by BRENDA team
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very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CFI1_MEDSA
222
0
23826
Swiss-Prot
other Location (Reliability: 3)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24000
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
1 * 24000, SDS-PAGE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor-diffusion method
hanging-drop vapor-diffusion method. 1.85 A resolution crystal structure of the enzyme in complex with (2S)-naringenin reveals an open-faced beta-sandwich fold
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Streptomyces venezuelae strain DHS2001
expression in Escherichia coli
expressed in Escherichia coli BL21 cells and in the Arabidopsis thaliana tt5 mutant
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isolation of cDNA
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ni, W.; Fahrendorf, T.; Ballance, G.M.; Lamb, C.J.; Dixon, R.A.
Stress responses in alfalfa (Medicago sativa L.) XX. Transcriptional activation of phenylpropanoid pathway genes in elicitor-induced cell suspension cultures
Plant Mol. Biol.
30
427-438
1996
Medicago sativa
Manually annotated by BRENDA team
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
Medicago sativa
Manually annotated by BRENDA team
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
Medicago sativa (P28012)
Manually annotated by BRENDA team
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
Medicago sativa
Manually annotated by BRENDA team
Hur, S.; Newby, Z.E.; Bruice, T.C.
Transition state stabilization by general acid catalysis, water expulsion, and enzyme reorganization in Medicago savita chalcone isomerase
Proc. Natl. Acad. Sci. USA
101
2730-2735
2004
Medicago sativa (P28012)
Manually annotated by BRENDA team
Ruiz-Pernia, J.J.; Silla, E.; Tunon, I.
Enzymatic effects on reactant and transition states. The case of chalcone isomerase
J. Am. Chem. Soc.
129
9117-9124
2007
Medicago sativa
Manually annotated by BRENDA team
Ruiz-Pernia, J.J.; Silla, E.; Tunon, I.
Comparative computational analysis of different active site conformations and substrates in a chalcone isomerase catalyzed reaction
J. Phys. Chem. B
110
20686-20692
2006
Medicago sativa (P28012)
Manually annotated by BRENDA team
Park, S.R.; Yoon, J.A.; Paik, J.H.; Park, J.W.; Jung, W.S.; Ban, Y.H.; Kim, E.J.; Yoo, Y.J.; Han, A.R.; Yoon, Y.J.
Engineering of plant-specific phenylpropanoids biosynthesis in Streptomyces venezuelae
J. Biotechnol.
141
181-188
2009
Medicago sativa (P28012), Medicago sativa
Manually annotated by BRENDA team
Cheng, A.X.; Zhang, X.; Han, X.J.; Zhang, Y.Y.; Gao, S.; Liu, C.J.; Lou, H.X.
Identification of chalcone isomerase in the basal land plants reveals an ancient evolution of enzymatic cyclization activity for synthesis of flavonoids
New Phytol.
217
909-924
2018
Medicago sativa, Marchantia paleacea, Selaginella moellendorffii, Physcomitrella appendiculatum
Manually annotated by BRENDA team