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Ligand UDP-L-rhamnose

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Amino sugar and nucleotide sugar metabolism

MetaCyc

alpha-solanine/alpha-chaconine biosynthesis, apigenin glycosides biosynthesis, eupatolitin 3-O-glucoside biosynthesis, hesperitin glycoside biosynthesis, isovitexin glycosides biosynthesis, kaempferide triglycoside biosynthesis, kaempferol glycoside biosynthesis (Arabidopsis), luteolin glycosides biosynthesis, naringenin glycoside biosynthesis, pelargonidin conjugates biosynthesis, quercetin glycoside biosynthesis (Arabidopsis), rutin biosynthesis, soybean saponin I biosynthesis, UDP-beta-L-rhamnose biosynthesis, violdelphin biosynthesis, vitexin and derivatives biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Natural Substrate (8 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

2.4.1.159

488625

UDPrhamnose + flavonol 3-O-glucoside = UDP + flavonol 3-O-rhamnosylglucoside

-

2.4.1.236

723433

UDP-L-rhamnose + diosmetin 7-O-glucoside = UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

723433

UDP-L-rhamnose + hesperetin 7-O-glucoside = UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

723433, 488818, 655963, 759382

UDP-L-rhamnose + naringenin 7-O-glucoside = UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

3 entries

2.4.1.273

715018

UDP-rhamnose + soyasaponin III = UDP + soyasaponin I

-

2.4.1.351

744243

UDP-beta-L-rhamnose + alpha-D-galacturonosyl-[(1->2)-alpha-L-rhamnosyl-(1->4)-alpha-D-galacturonosyl]n = UDP + [(1->2)-alpha-L-rhamnosyl-(1->4)-alpha-D-galacturonosyl]n+1

-

2.4.1.B53

723433

UDP-L-rhamnose + hesperetin 7-O-beta-D-glucoside = UDP + hesperetin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433

UDP-L-rhamnose + naringenin 7-O-beta-D-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

2 entries

Substrate in Enzyme-catalyzed Reactions (29 results)

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Show Substrate (29 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

2.4.1.159

659272

UDP-L-rhamnose + kaempferol = kaempferol-3-O-rhamnoside + UDP

-

2.4.1.159

659272

UDP-L-rhamnose + quercetin = quercetin-3-O-rhamnoside + UDP

-

2.4.1.159

488625

UDPrhamnose + flavonol 3-O-diglycoside = UDP + flavonol 3-O-triglycoside

-

2.4.1.159

488625

UDPrhamnose + flavonol 3-O-glucoside = UDP + flavonol 3-O-rhamnosylglucoside

-

2.4.1.236

488818

UDP-L-rhamnose + a flavanone 7-O-glucoside = UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

655963

UDP-L-rhamnose + apigenin 7-O-glucoside = UDP + apigenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

723433

UDP-L-rhamnose + diosmetin 7-O-glucoside = UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

655963, 723433, 488818

UDP-L-rhamnose + hesperetin 7-O-glucoside = UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

655963

UDP-L-rhamnose + luteolin 7-O-glucoside = UDP + luteolin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

655963, 488818, 723433, 759382

UDP-L-rhamnose + naringenin 7-O-glucoside = UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]

-

2.4.1.236

735522

UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside = UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]

-

2.4.1.236

735522

UDP-beta-L-rhamnose + naringenin-7-O-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]

-

2.4.1.273

715018

UDP-rhamnose + soyasaponin III = UDP + soyasaponin I

-

2.4.1.273

759939

UDP-beta-L-rhamnose + soyasaponin III = UDP + soyasaponin I

-

2.4.1.159

4 entries

2.4.1.236

8 entries

2.4.1.273

2 entries

2.4.1.351

744243

UDP-beta-L-rhamnose + alpha-D-galacturonosyl-[(1->2)-alpha-L-rhamnosyl-(1->4)-alpha-D-galacturonosyl]n = UDP + [(1->2)-alpha-L-rhamnosyl-(1->4)-alpha-D-galacturonosyl]n+1

-

2.4.1.384

761686

UDP-beta-L-rhamnose + 3-dichloroaniline = 3-dichloroaniline 3-O-beta-L-rhamnoside + UDP

-

2.4.1.384

761686

UDP-beta-L-rhamnose + 3-dichlorobenzenethiol = 3-dichlorobenzenethiol 3-O-beta-L-rhamnoside + UDP

-

2.4.1.384

761686

UDP-beta-L-rhamnose + 3-dichlorophenol = 3-dichlorophenol 3-O-beta-L-rhamnoside + UDP

-

2.4.1.B53

723433

UDP-L-rhamnose + cyanidin 3-O-beta-D-glucoside = UDP + cyanidin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433

UDP-L-rhamnose + diosmetin 7-O-beta-D-glucoside = UDP + diosmetin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433

UDP-L-rhamnose + hesperetin 7-O-beta-D-glucoside = UDP + hesperetin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

737014

UDP-L-rhamnose + kaempferol 3-O-beta-D-galactoside = UDP + kaempferol 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-galactoside]

-

2.4.1.B53

723433, 737014

UDP-L-rhamnose + kaempferol 3-O-beta-D-glucoside = UDP + kaempferol 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433

UDP-L-rhamnose + kaempferol 7-O-beta-D-glucoside = UDP + kaempferol 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433, 735522

UDP-L-rhamnose + naringenin 7-O-beta-D-glucoside = UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433

UDP-L-rhamnose + peonidin 3-O-beta-D-glucoside = UDP + peonidin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

-

2.4.1.B53

723433, 735522

UDP-L-rhamnose + quercetin 3-O-beta-D-glucoside = UDP + quercetin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

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2.4.1.B53

737014

UDP-L-rhamnose + quercetin 7-O-beta-D-galactoside = UDP + quercetin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-galactoside]

-

2.4.1.B53

737014, 723433

UDP-L-rhamnose + quercetin 7-O-beta-D-glucoside = UDP + quercetin 7-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

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2.4.1.384

3 entries

2.4.1.B53

11 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.1.1.133

-

UDP-4-keto-6-deoxy-D-glucose + NADPH + H+ = UDP-L-rhamnose + NADP+

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1.1.1.133

-

UDP-4-dehydro-6-deoxy-D-glucose + NADPH = UDP-beta-L-rhamnose + NADP+

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1.1.1.133

2 entries

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

feedback inhibition of UGD, 50% inhibition at 0.1 mM

4.2.1.76

716065

-

feedback inhibition of UGD, 60% inhibition at 0.1 mM

4.2.1.76

716065

-

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

pH 7.5, 37°C, cosubstrate hesperetin 7-O-glucoside

2.4.1.236

0.0011

-

655963

pH 7.5, 37°C, cosubstrate naringenin 7-O-glucoside

2.4.1.236

0.0013

-

655963

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

488625

-

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

1982

Kleinehollenhorst, G.; Behrens, H.; Pegels, G.; Strunk, N.; Wiermann, R.

Z. Naturforsch. C

37c

587-599

488818

16667183

Flavanone glycoside biosynthesis in Citrus. Chalcone synthase, UDP-glucose: flavanone-7-O-glucosyltransferase and -rhamnosyltransferase activities in cell-free extracts

1989

Lewinsohn, E.; Britsch, L.; Mazur, Y.; Gressel, J.

Plant Physiol.

91

1323-1328

655963

1939145

UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus

1991

Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.

J. Biol. Chem.

266

20953-20959

659272

12900416

UGT73C6 and UGT78D1, gycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana

2003

Jones, P.; Messner, B.; Nakajima, J.I.; Schaeffner, A.R.; Saito, K.

J. Biol. Chem.

278

43910-43918

715018

20350545

Identification and characterization of glycosyltransferases involved in the biosynthesis of soyasaponin I in Glycine max

2010

Shibuya, M.; Nishimura, K.; Yasuyama, N.; Ebizuka, Y.

FEBS Lett.

584

2258-2264

716065

20538863

Identification of an L-rhamnose synthetic pathway in two nucleocytoplasmic large DNA viruses

2010

Parakkottil Chothi, M.; Duncan, G.; Armirotti, A.; Abergel, C.; Gurnon, J.; Van Etten, J.; Bernardi, C.; Damonte, G.; Tonetti, M.

J. Virol.

84

8829-8838

723433

22989156

The molecular and enzymatic basis of bitter/non-bitter flavor of citrus fruit: evolution of branch-forming rhamnosyltransferases under domestication

2013

Frydman, A.; Liberman, R.; Huhman, D.V.; Carmeli-Weissberg, M.; Sapir-Mir, M.; Ophir, R.; W Sumner, L.; Eyal, Y.

Plant J.

73

166-178

735522

26433966

Substrate preference of citrus naringenin rhamnosyltransferases and their application to flavonoid glycoside production in fission yeast

2016

Ohashi, T.; Hasegawa, Y.; Misaki, R.; Fujiyama, K.

Appl. Microbiol. Biotechnol.

100

687-696

737014

24072327

Linkage mapping, molecular cloning and functional analysis of soybean gene Fg2 encoding flavonol 3-O-glucoside (1->6) rhamnosyltransferase

2014

Rojas Rodas, F.; Rodriguez, T.; Murai, Y.; Iwashina, T.; Sugawara, S.; Suzuki, M.; Nakabayashi, R.; Yonekura-Sakakibara, K.; Saito, K.; Kitajima, J.; Toda, K.; Takahashi, R.

Plant Mol. Biol.

84

287-300

744243

28283389

Biochemical characterization of rhamnosyltransferase involved in biosynthesis of pectic rhamnogalacturonan I in plant cell wall

2017

Uehara, Y.; Tamura, S.; Maki, Y.; Yagyu, K.; Mizoguchi, T.; Tamiaki, H.; Imai, T.; Ishii, T.; Ohashi, T.; Fujiyama, K.; Ishimizu, T.

Biochem. Biophys. Res. Commun.

486

130-136

759382

27808514

Variation in key flavonoid biosynthetic enzymes and phytochemicals in Rio Red Grapefruit (Citrus paradisi Macf.) during fruit development

2016

Chaudhary, P.R.; Bang, H.; Jayaprakasha, G.K.; Patil, B.S.

J. Agric. Food Chem.

64

9022-9032

759939

29401289

Isolation and characterization of the soybean Sg-3 gene that is involved in genetic variation in sugar chain composition at the C-3 position in soyasaponins

2018

Yano, R.; Takagi, K.; Tochigi, S.; Fujisawa, Y.; Nomura, Y.; Tsuchinaga, H.; Takahashi, Y.; Takada, Y.; Kaga, A.; Anai, T.; Tsukamoto, C.; Seki, H.; Muranaka, T.; Ishimoto, M.

Plant Cell Physiol.

59

792-805

761686

32238768

Exploring the nucleophilic N-and S-glycosylation capacity of Bacillus licheniformis Yjic enzyme

2020

Bashyal, P.; Thapa, S.; Kim, T.; Pandey, R.; Sohng, J.

J. Microbiol. Biotechnol.

30

1092-1096

Links to other databases for UDP-L-rhamnose

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Show Links (1 entry)

ChEBI

PubChem

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