Flavonol 3-O-glucosyltransferase

Short description: Class of enzymes

Flavonol 3-O-glucosyltransferase

Identifiers
EC number| 2.4.1.91
CAS number| 50812-18-5
Databases
IntEnz| IntEnz view
BRENDA| BRENDA entry
ExPASy| NiceZyme view
KEGG| KEGG entry
MetaCyc| metabolic pathway
PRIAM| profile
PDB structures| RCSB PDB PDBe PDBsum
Gene Ontology| AmiGO  / QuickGO
| Search

PMC| articles
PubMed| articles
NCBI| proteins

Flavonol 3-O-glucosyltransferase (EC 2.4.1.91) is an enzyme that catalyzes the general chemical reaction

UDP-glucose + a flavonol ⇌ UDP + a flavonol 3-O-beta-D-glucoside

The two substrates of this enzyme are UDP-glucose and a flavonol. Its products are uridine diphosphate (UDP) and the corresponding flavonol 3-O-beta-D-glucoside. The flavonoids that can act as substrates within this reaction include quercetin, kaempferol, dihydrokaempferol, kaempferid, fisetin, and isorhamnetin. Flavonol 3-O-glucosyltransferase is a hexosyl group transfer enzyme.[1]

This enzyme is known by the systematic name UPD-glucose:flavonol 3-O-D glucosyltransferase, and it participates in flavonoid biosynthesis and causes the formation of anthocyanins. Anthocyanins produce a purple color in the plant tissues that they are present in.[2]

## Contents

* 1 Occurence
* 2 Function
* 3 Nomenclature
* 4 Inhibitors and Structure of the Enzyme
* 5 References

## Occurence

Flavonol 3-O-glucosyltransferase is found in grapes (Vitis vinifera),[3] parsley,[4] snapdragons (Antirrhinum majus), kale (Brassica oleracea), tulip bulbs,[5] peony,[6] and grapefruit (Citrus x paradisi).[7]

## Function

This enzyme is involved in the biosynthesis of secondary metabolites. The primary function of this enzyme within its pathway is binding a glucoside onto a flavonol molecule, forming a flavonol 3-O-glucoside. For example, it converts quercetin to isoquercetin:[1]

1. REDIRECT Template:Chemical reaction

A glucose unit is transferred from UDP-glucose to a specific hydroxy group of the flavonol, with uridine diphosphate (UDP) as a byproduct. By the same mechanism, the enzyme converts anthocyanidins to anthocyanins as a part of the phenylpropanoid pathway. For example, pelargonidin is transformed into callistephin (pelargonidin 3-O-glucoside).

1. REDIRECT Template:Chemical reaction

This enzyme is also involved in the flavone glycoside pathway, and daphnetin modification in some organisms.[8]

## Nomenclature

This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP-glucose:flavonol 3-O-D-glucosyltransferase. Other names in common use include:

* GTI,
* uridine diphosphoglucose-flavonol 3-O-glucosyltransferase,
* UDP-glucose:flavonol 3-O-glucosyltransferase, and
* UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT).[8]

Among those, UFGT is divided into UDP-glucose: Flavonoid 3-O-glucosyltransferase (UF3GT) and UDP-glucose: Flavonoid 5-O-glucosyltransferase (UF5GT), which are responsible for the glucosylation of anthocyanins to produce stable molecules.[6]

## Inhibitors and Structure of the Enzyme

Some of the inhibitors of this enzyme include CaCl2, CoCl2, Cu+2, CuCl2, KCl, Mg+2, and Mn+2.[9] The primary active site residue of this enzyme is Asp181, as determined by studies of how mutations affect enzyme capacity.[10] There are several documentations of the crystalline structure of flavonol 3-O-glucosyltransferase (2C1X, 2C1Z, and 2C9Z),[11] and, based on these renderings of the enzyme, there is only one subunit in the quaternary structure of the molecule.

## References

1. ↑ 1.0 1.1 Kleinehollenhorst, G.; Behrens, H.; Pegels, G.; Srunk, N.; Wiermann, R. (1982). "Formation of Flavonol 3-O-Diglycosides and Flavonol 3-O-Triglycosides by Enzyme Extracts from Anthers of Tulipa cv. Apeldoorn / Characterization and Activity of Three Different O -Glycosyltransferases during Anther Development". Zeitschrift für Naturforschung C 37 (7–8): 587–599. doi:10.1515/znc-1982-7-808.
2. ↑ Dooner, H. K.; Nelson, O. E. (1977). "Genetic control of UDPglucose:flavonol 3-O-glucosyltransferase in the endosperm of maize". Biochemical Genetics 15 (5–6): 509–519. doi:10.1007/BF00520194. PMID 880210.
3. ↑ "Comparison of UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT) gene sequences between white grapes (Vitis vinifera) and their sports with red skin". Plant Sci. 160 (3): 543–550. February 2001. doi:10.1016/S0168-9452(00)00425-8. PMID 11166442. Bibcode: 2001PlnSc.160..543K.
4. ↑ "UDP-glucose: flavonol 3-0-glucosyltransferase from cell suspension cultures of parsley". Biochim. Biophys. Acta 309 (2): 289-95. 1973. doi:10.1016/0005-2744(73)90027-2. PMID 4731963.
5. ↑ Wiermann R (1982). "Formation of flavonol 3-O-diglycosides and flavonol 3-O-triglycosides by enzyme extracts from anthers of Tulipa cv apeldoorn - characterization and activity of 3 different O-glycosyltransferases during anther development". Z. Naturforsch. C 37: 587-599. doi:10.1515/znc-1982-7-808.
6. ↑ 6.0 6.1 "Isolation of a UDP-glucose: Flavonoid 5-O-glucosyltransferase gene and expression analysis of anthocyanin biosynthetic genes in herbaceous peony (Paeonia lactiflora Pall.)". Electronic Journal of Biotechnology 15 (6). November 2012. doi:10.2225/vol15-issue6-fulltext-7.
7. ↑ "BRENDA - Information on EC 2.4.1.91 - flavonol 3-O-glucosyltransferase". https://www.brenda-enzymes.org/enzyme.php?ecno=2.4.1.91.
8. ↑ 8.0 8.1 Enzyme 2.4.1.91 at KEGG Pathway Database.
9. ↑ "Flavonol 3-O-glucosyltransferase". Springer Handbook of Enzymes. 32. Springer Berlin Heidelberg. 1 January 2006. pp. 21–29. doi:10.1007/978-3-540-49534-5_2. ISBN 978-3-540-32591-8.
10. ↑ Hiromoto, Takeshi; Honjo, Eijiro; Noda, Naonobu; Tamada, Taro; Kazuma, Kohei; Suzuki, Masahiko; Blaber, Michael; Kuroki, Ryota (2016-12-06). "Structural basis for acceptor-substrate recognition of UDP-glucose: anthocyanidin 3-O-glucosyltransferase from Clitoria ternatea". Protein Science 24 (3): 395–407. doi:10.1002/pro.2630. ISSN 0961-8368. PMID 25556637.
11. ↑ Offen, W; Martinez-Fleites, C; Yang, M; Kiat-Lim, E; Davis, B.G; Tarling, C.A; Ford, C.M; Bowles, D.J et al. (2006-01-01). "Structure of a Flavonoid Glucosyltransferase Reveals the Basis for Plant Natural Product Modification.". EMBO J. 25 (6): 1396–405. doi:10.1038/sj.emboj.7600970. PMID 16482224. PMC 1422153. https://www.rcsb.org/pdb/explore.do?structureId=2c1z.

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Transferases: glycosyltransferases (EC 2.4)

2.4.1: Hexosyl-
transferases|

| Glucosyl-|

* Phosphorylase
* Starch
* Glycogen
* Myo-
* Glycogen synthase
* Debranching enzyme
* Branching enzyme
* 1,3-Beta-glucan synthase
* Ceramide glucosyltransferase
* N-glycosyltransferase

|

Galactosyl-|

* Lactose synthase
* B-N-acetylglucosaminyl-glycopeptide b-1,4-galactosyltransferase
* Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase (C1GALT1)

Glucuronosyl-|

* B3GAT1
* B3GAT2
* B3GAT3

* UGT1A1
* UGT1A3
* UGT1A4
* UGT1A5
* UGT1A6
* UGT1A7
* UGT1A8
* UGT1A9
* UGT1A10

* UGT2A1
* UGT2A2
* UGT2A3
* UGT2B4
* UGT2B7
* UGT2B10
* UGT2B11
* UGT2B15
* UGT2B17
* UGT2B28

* Hyaluronan synthase: HAS1
* HAS2
* HAS3

Fucosyl-|

* POFUT1
* POFUT2
* FUT1
* FUT2
* FUT3
* FUT4
* FUT5
* FUT6
* FUT7
* FUT8
* FUT9
* FUT10
* FUT11

Mannosyl-|

* Dolichyl-phosphate-mannose-protein mannosyltransferase
* POMT1
* POMT2
* DPM1
* DPM3

* ALG1
* ALG2
* ALG3
* ALG6
* ALG8
* ALG9
* ALG12

2.4.2: Pentosyl-
transferases|

| Ribose|

| ADP-ribosyltransferase|

* diphthamide ADP-ribosyltransferase
* Diphtheria toxin
* Pseudomonas exotoxin

* arginine ADP-ribosyltransferase
* Pertussis toxin
* Cholera toxin

* Poly ADP ribose polymerase

* Sirtuin

|

Phosphoribosyltransferase|

* Adenine phosphoribosyltransferase
* Hypoxanthine-guanine phosphoribosyltransferase
* Uracil phosphoribosyltransferase
* Amidophosphoribosyltransferase

Other|

* Purine nucleoside phosphorylase: Thymidine phosphorylase
* ECGF1

Other|

* Xylosyltransferase
* XYLT1
* XYLT2
* Arabinosyltransferase
* Indolylacetylinositol arabinosyltransferase

2.4.99: Sialyl
transferases|

* Beta-galactoside alpha-2,6-sialyltransferase
* Monosialoganglioside sialyltransferase
* ST8SIA4

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Enzymes

Activity|

* Active site
* Binding site
* Catalytic triad
* Oxyanion hole
* Enzyme promiscuity
* Catalytically perfect enzyme
* Coenzyme
* Cofactor
* Enzyme catalysis

Regulation|

* Allosteric regulation
* Cooperativity
* Enzyme inhibitor
* Enzyme activator

Classification|

* EC number
* Enzyme superfamily
* Enzyme family
* List of enzymes

Kinetics|

* Enzyme kinetics
* Eadie–Hofstee diagram
* Hanes–Woolf plot
* Lineweaver–Burk plot
* Michaelis–Menten kinetics

Types|

* EC1 Oxidoreductases (list)
* EC2 Transferases (list)
* EC3 Hydrolases (list)
* EC4 Lyases (list)
* EC5 Isomerases (list)
* EC6 Ligases (list)
* EC7 Translocases (list)

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