Chalcone isomerase

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chalcone isomerase
Identifiers
EC no. 5.5.1.6
CAS no. 9073-57-8
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BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
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NCBI proteins
Chalcone isomerase
PDB 1jep EBI.jpg
chalcone isomerase complexed with 4'-hydroxyflavanone
Identifiers
SymbolChalcone
Pfam PF02431
InterPro IPR003466
SCOP2 1eyp / SCOPe / SUPFAM
Available protein structures:
Pfam   structures / ECOD  
PDB RCSB PDB; PDBe; PDBj
PDBsum structure summary

In enzymology, a chalcone isomerase (EC 5.5.1.6) is an enzyme that catalyzes the chemical reaction

Contents

a chalcone a flavanone

Hence, this enzyme has one substrate, a chalcone, and one product, a flavanone.

This enzyme belongs to the family of isomerases, specifically the class of intramolecular lyases. The systematic name of this enzyme class is flavanone lyase (decyclizing). This enzyme is also called chalcone-flavanone isomerase. This enzyme participates in flavonoid biosynthesis.

The Petunia hybrida (Petunia) genome contains two genes coding for very similar enzymes, ChiA and ChiB, but only the first seems to encode a functional chalcone isomerase.

Structural studies

As of late 2007, 7 structures have been solved for this class of enzymes, with PDB accession codes 1EYP, 1EYQ, 1FM7, 1FM8, 1JEP, 1JX0, and 1JX1.

Chalcone isomerase has a core 2-layer alpha/beta structure consisting of beta(3)-alpha(2)-beta-alpha(2)-beta(3). [1]

Related Research Articles

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Enoyl-CoA-(∆) isomerase (EC 5.3.3.8, also known as dodecenoyl-CoA- isomerase, 3,2-trans-enoyl-CoA isomerase, ∆3 ,∆2 -enoyl-CoA isomerase, or acetylene-allene isomerase, is an enzyme that catalyzes the conversion of cis- or trans-double bonds of coenzyme A bound fatty acids at gamma-carbon to trans double bonds at beta-carbon as below:

<span class="mw-page-title-main">Rutin</span> Chemical compound

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<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">Apigenin</span> Chemical compound

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

<span class="mw-page-title-main">Flavones</span> Class of flavonoid chemical compounds

Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

<span class="mw-page-title-main">Flavanone</span>

The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides.

<span class="mw-page-title-main">Chalcone synthase</span>

Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a class of organic compounds found mainly in plants as natural defense mechanisms and as synthetic intermediates. CHS was the first type III PKS to be discovered. It is the first committed enzyme in flavonoid biosynthesis. The enzyme catalyzes the conversion of 4-coumaroyl-CoA and malonyl-CoA to naringenin chalcone.

In enzymology, a 3-carboxy-cis,cis-muconate cycloisomerase is an enzyme that catalyzes the chemical reaction

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<span class="mw-page-title-main">Chloromuconate cycloisomerase</span>

In enzymology, a chloromuconate cycloisomerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

In enzymology, a glucose-6-phosphate 1-epimerase is an enzyme that catalyzes the chemical reaction

In enzymology, a muconolactone Δ-isomerase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Phosphoenolpyruvate mutase</span> Enzyme

In enzymology, a phosphoenolpyruvate mutase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Indole-3-glycerol-phosphate synthase</span> Class of enzymes

The enzyme indole-3-glycerol-phosphate synthase (IGPS) (EC 4.1.1.48) catalyzes the chemical reaction

The enzyme hydroperoxide dehydratase (EC 4.2.1.92) catalyzes the chemical reaction

<span class="mw-page-title-main">Tricin</span> Chemical compound

Tricin is a chemical compound. It is an O-methylated flavone, a type of flavonoid. It can be found in rice bran and sugarcane.

<span class="mw-page-title-main">Chalconoid</span> Natural phenols related to chalcone

Chalconoids, also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important biological compounds.

References

  1. Jez JM, Bowman ME, Dixon RA, Noel JP (September 2000). "Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase". Nat. Struct. Biol. 7 (9): 786–91. doi:10.1038/79025. PMID   10966651. S2CID   22198011.

Further reading

This article incorporates text from the public domain Pfam and InterPro: IPR003466