print visible entries

print all entries

Ligand dTDP-beta-L-rhamnose

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

dTDPLrhamnose biosynthesis, elloramycin biosynthesis, ginsenoside metabolism

KEGG

Arabinogalactan biosynthesis - Mycobacterium, Biosynthesis of nucleotide sugars, Biosynthesis of secondary metabolites, O-Antigen nucleotide sugar biosynthesis, Polyketide sugar unit biosynthesis, Streptomycin biosynthesis more

MetaCyc

acetan biosynthesis, dimycocerosyl triglycosyl phenolphthiocerol biosynthesis, dTDP-beta-L-rhamnose biosynthesis, elloramycin biosynthesis, Escherichia coli serotype O:107 O antigen biosynthesis, Escherichia coli serotype O:117 O antigen biosynthesis, Escherichia coli serotype O:149/Shigella boydii serotype O1 O antigen biosynthesis, Escherichia coli serotype O:152 O antigen biosynthesis, Escherichia coli serotype O:177 O antigen biosynthesis, Escherichia coli serotype O:1B/Salmonella enterica serotype O:42 O antigen biosynthesis, Escherichia coli serotype O:2 O antigen biosynthesis, Escherichia coli serotype O:49 O antigen biosynthesis, Escherichia coli serotype O:50 O antigen biosynthesis, Escherichia coli serotype O:51/Salmonella enterica serotype O:57 O antigen biosynthesis, Escherichia coli serotype O:7 O antigen biosynthesis, Escherichia coli serotype O:71/Salmonella enterica serotype O:28ac O antigen biosynthesis, ginsenosides biosynthesis, K-252 biosynthesis, maysin biosynthesis, mycolyl-arabinogalactan-peptidoglycan complex biosynthesis, p-HBAD biosynthesis, Porphyromonas gingivalis O-LPS antigen biosynthesis, rhamnolipid biosynthesis, Salmonella enterica serotype O:2 O antigen biosynthesis, Salmonella enterica serotype O:3,10 O antigen biosynthesis, Salmonella enterica serotype O:4 O antigen biosynthesis (group B1), Salmonella enterica serotype O:8 O antigen biosynthesis, Salmonella enterica serotype O:9 O antigen biosynthesis, Salmonella enterica serotype O:9,46 O antigen biosynthesis, Salmonella enterica serotype O:9,46,27 O antigen biosynthesis, spinosyn biosynthesis, streptomycin biosynthesis more

Show all BRENDA pathways known for dTDP-beta-L-rhamnose

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

top print hide

Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.133

dTDP-6-deoxy-L-mannose + NADP+ = dTDP-4-dehydro-6-deoxy-L-mannose + NADPH

668041, 661486

1kc3, 3D-view

1.1.1.133

dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+

741022, 741309

1kc3, 3D-view

1.1.1.133

2 entries

2.4.1.289

dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol

714160, 720888, 720385

-

2.4.1.331

dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C = dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C

724728

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.133

dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+ = dTDP-beta-L-rhamnose + NADP+

0

1kc3, 3D-view

1.1.1.133

dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH = dTDP-L-rhamnose + NADP+

285844

1kc3, 3D-view

5.1.3.13

TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose = TDP-L-rhamnose

0

2ixc, 3D-view

5.1.3.13

TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose = TDP-L-rhamnose

0

2ixl, 3D-view

1.1.1.133

2 entries

5.1.3.13

2 entries

5.1.3.25

dTDP-6-deoxy-beta-L-talose = dTDP-beta-L-rhamnose

0

-

Substrate in Enzyme-catalyzed Reactions (11 results)

top print hide

Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.133

dTDP-6-deoxy-L-mannose + NADP+ = dTDP-4-dehydro-6-deoxy-L-mannose + NADPH

661486, 668041

1kc3, 3D-view

1.1.1.133

dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+

741022, 741309

1kc3, 3D-view

1.1.1.133

2 entries

2.4.1.277

dTDP-L-rhamnose + 10-deoxymethynolide = dTDP + L-rhamnosyl-10-deoxymethynolide

736536

-

2.4.1.289

dTDP-6-deoxy-beta-L-mannose + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol = dTDP + alpha-L-rhamnopyranosyl-(1->3)-N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol

720385, 714160, 720888

-

2.4.1.289

dTDP-beta-L-rhamnose + GlcNAc-diphospho-trans,octacis-decaprenol = ?

719822

-

2.4.1.289

2 entries

2.4.1.331

dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C = dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C

729367, 724728

-

2.4.1.377

dTDP-beta-L-rhamnose + alpha-D-galactosyl-diphospho-ditrans,octacis-undecaprenol = dTDP + alpha-L-Rha-(1->3)-alpha-D-Gal-PP-undecaprenol

761365

-

2.4.1.381

dTDP-beta-L-rhamnose + alpha-D-Man-(1->2)-alpha-D-Man-(1->3)-alpha-D-Gal-PP-undecaprenol = dTDP + alpha-L-Rha-(1->2)-alpha-D-Man-(1->2)-alpha-D-Man-(1->3)-alpha-D-Gal-PP-undecaprenol

761365

-

2.4.1.384

dTDP-L-rhamnose + 3-hydroxyflavone = 3-hydroxyflavone 3-O-beta-D-rhamnoside + dTDP

761013

-

2.4.1.384

TDP-L-rhamnose + resveratrol = TDP + resveratrol 3-O-beta-L-rhamnoside

760385

-

2.4.1.384

2 entries

2.4.1.81

dTDP-beta-L-rhamnose + genistein = dTDP + 7-O-(alpha-L-rhamnopyranosyl)genistein

758337

-

Product in Enzyme-catalyzed Reactions (9 results)

top print hide

Show Product (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.133

dTDP-4-dehydro-6-deoxy-D-glucose + NADH + H+ = dTDP-beta-L-rhamnose + NAD+

0

1kc3, 3D-view

1.1.1.133

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

0

1kc3, 3D-view

1.1.1.133

dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+ = dTDP-beta-L-rhamnose + NADP+

0

1kc3, 3D-view

1.1.1.133

dTDP-4-dehydro-6-deoxy-D-glucose + NADPH + H+ = dTDP-L-rhamnose + NADP+

285843

1kc3, 3D-view

1.1.1.133

dTDP-6-deoxy-L-lyxo-4-hexulose + NAD(P)H = dTDP-L-rhamnose + NAD(P)+

285846

1kc3, 3D-view

1.1.1.133

dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH = dTDP-L-rhamnose + NADP+

285845, 285844

1kc3, 3D-view

5.1.3.13

TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose = TDP-L-rhamnose

0

2ixc, 3D-view

5.1.3.13

TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose = TDP-L-rhamnose

0

2ixl, 3D-view

1.1.1.133

6 entries

5.1.3.13

2 entries

5.1.3.25

dTDP-6-deoxy-beta-L-talose = dTDP-beta-L-rhamnose

0

-

Inhibitor in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.302

-

721589

-

2.7.7.24

-

643084

1g3l, 3D-view

2.7.7.24

-

643084

5ify, 3D-view

2.7.7.24

-

643084

6n0u, 3D-view

2.7.7.24

3 entries

2.7.7.9

-

643748

-

3D Structure of Enzyme-Ligand-Complex (PDB) (36 results)

top print hide

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (36 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.133

1kc3, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

2.7.7.24

1g3l, 3D-view

2.7.7.24

5ify, 3D-view

2.7.7.24

6n0u, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

5.1.3.13

2ixc, 3D-view

5.1.3.13

2ixl, 3D-view

2.7.7.24

21 entries

5.1.3.13

14 entries

Enzyme Kinetic Parameters

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.302

0.0835

-

pH 6.0, 22°C

721589

References & Links

Literature References (22)

top print hide

Show Reference (22 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285843

4384782

The mechanism of 6-deoxyhexose synthesis. II. Conversion of deoxythymidine diphosphate 4-keto-6-deoxy-D-glucose to deoxythymidine diphosphate L-rhamnose

1968

Melo, A.; Glaser, L.

J. Biol. Chem.

243

1475-1478

285844

-

Overexpression, purification, crystallization and preliminary structural study of dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD), the fourth enzyme of the dTDP-L-rhamnose synthesis pathway, from Salmonella enterica serovar typhimurium

1999

Giraud, M.F.; McMiken, H.J.; Leonard, G.A.; Messner, P.; Whitfield, C.; Naismith, J.H.

Acta Crystallogr. Sect. D

55

2043-2046

285845

10702238

Thymidine diphosphate-6-deoxy-L-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-L-talose from Actinobacillus actinomycetemcomitans

2000

Nakano, Y.; Suzuki, N.; Yoshida, Y.; Nezu, T.; Yamashita, Y.; Koga, T.

J. Biol. Chem.

275

6806-6812

285846

10455186

Characterization of dTDP-4-dehydrorhamnose 3,5-epimerase and dTDP-4-dehydrorhamnose reductase, required for dTDP-L-rhamnose biosynthesis in Salmonella enterica serovar typhimurium LT2

1999

Graninger, M.; Nidetzky, B.; Heinrichs, D.E.; Whitfield, C.; Messner, P.

J. Biol. Chem.

274

25069-25077

643084

11118200

The structural basis of the catalytic mechanism and regulation of glucose-1-phosphate thymidylyltransferase (RmlA)

2000

Blankenfeldt, W.; Asuncion, M.; Lam, J.S.; Naismith, J.H.

EMBO J.

19

6652-6663

643748

-

Uridine diphosphoryl glucose pyrophosphorylase

1973

Turnquist, R.L.; Hansen, R.G.

The Enzymes, 3rd. Ed. (Boyer, P. D. , ed. )

8

51-71

661486

15977277

An enzyme module system for the synthesis of dTDP-activated deoxysugars from dTMP and sucrose

2005

Elling, L.; Rupprath, C.; Gunther, N.; Romer, U.; Verseck, S.; Weingarten, P.; Drager, G.; Kirschning, A.; Piepersberg, W.

ChemBioChem

6

1423-1430

668041

16276532

Preparative synthesis of dTDP-L-rhamnose through combined enzymatic pathways

2005

Kang, Y.; Yang, Y.; Lee, K.; Lee, S.; Sohng, J.K.; Lee, H.C.; Liou, K.; Kim, B.

Biotechnol. Bioeng.

93

21-27

714160

17087520

In vitro biosynthesis of UDP-N,N'-diacetylbacillosamine by enzymes of the Campylobacter jejuni general protein glycosylation system

2006

Olivier, N.B.; Chen, M.M.; Behr, J.R.; Imperiali, B.

Biochemistry

45

13659-13669

719822

15294902

Inactivation of the mycobacterial rhamnosyltransferase, which is needed for the formation of the arabinogalactan-peptidoglycan linker, leads to irreversible loss of viability

2004

Mills, J.A.; Motichka, K.; Jucker, M.; Wu, H.P.; Uhlik, B.C.; Stern, R.J.; Scherman, M.S.; Vissa, V.D.; Pan, F.; Kundu, M.; Ma, Y.F.; McNeil, M.

J. Biol. Chem.

279

43540-43546

720385

19047740

Development of a microtitre plate-based assay for lipid-linked glycosyltransferase products using the mycobacterial cell wall rhamnosyltransferase WbbL

2008

Grzegorzewicz, A.E.; Ma, Y.; Jones, V.; Crick, D.; Liav, A.; McNeil, M.R.

Microbiology

154

3724-3730

720888

16186480

In vitro assembly of the undecaprenylpyrophosphate-linked heptasaccharide for prokaryotic N-linked glycosylation

2005

Glover, K.J.; Weerapana, E.; Imperiali, B.

Proc. Natl. Acad. Sci. USA

102

14255-14259

721589

12680772

Initial characterization of novobiocic acid noviosyl transferase activity of NovM in biosynthesis of the antibiotic novobiocin

2003

Freel Meyers, C.L.; Oberthür, M.; Anderson, J.W.; Kahne, D.; Walsh, C.T.

Biochemistry

42

4179-4189

724728

11306350

Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin

2001

Blanco, G.; Patallo, E.P.; Brana, A.F.; Trefzer, A.; Bechthold, A.; Rohr, J.; Mendez, C.; Salas, J.A.

Chem. Biol.

8

253-263

729367

22361136

Ketoolivosyl-tetracenomycin C: a new ketosugar bearing tetracenomycin reveals new insight into the substrate flexibility of glycosyltransferase ElmGT

2012

Nybo, S.E.; Shabaan, K.A.; Kharel, M.K.; Sutardjo, H.; Salas, J.A.; Mendez, C.; Rohr, J.

Bioorg. Med. Chem. Lett.

22

2247-2250

736536

23770075

Combinatorial biosynthesis and antibacterial evaluation of glycosylated derivatives of 12-membered macrolide antibiotic YC-17

2013

Shinde, P.B.; Han, A.R.; Cho, J.; Lee, S.R.; Ban, Y.H.; Yoo, Y.J.; Kim, E.J.; Kim, E.; Song, M.C.; Park, J.W.; Lee, D.G.; Yoon, Y.J.

J. Biotechnol.

168

142-148

741022

26278404

GacA is essential for group A Streptococcus and defines a new class of monomeric dTDP-4-dehydrorhamnose reductases (RmlD)

2015

van der Beek, S.L.; Le Breton, Y.; Ferenbach, A.T.; Chapman, R.N.; van Aalten, D.M.; Navratilova, I.; Boons, G.J.; McIver, K.S.; van Sorge, N.M.; Dorfmueller, H.C.

Mol. Microbiol.

98

946-962

741309

24831810

Haloferax volcanii N-glycosylation: delineating the pathway of dTDP-rhamnose biosynthesis

2014

Kaminski, L.; Eichler, J.

PLoS ONE

9

e97441

758337

-

Biosynthesis of natural and non-natural genistein glycosides

2017

Parajuli, P.; Pandey, R.; Huyen Nguyen, T.; Shrestha, B.; Yamaguchi, T.; Sohng, J.

RSC Adv.

7

16217-16231

760385

25239890

Enzymatic biosynthesis of novel resveratrol glucoside and glycoside derivatives

2014

Pandey, R.; Parajuli, P.; Shin, J.; Lee, J.; Lee, S.; Hong, Y.; Park, Y.; Kim, J.; Sohng, J.

Appl. Environ. Microbiol.

80

7235-7243

761013

27444326

Donor specificity of YjiC glycosyltransferase determines the conjugation of cytosolic NDP-sugar in in vivo glycosylation reactions

2016

Pandey, R.; Parajuli, P.; Gurung, R.; Sohng, J.

Enzyme Microb. Technol.

91

26-33

761365

7684736

Glycosyl transferases of O-antigen biosynthesis in Salmonella enterica Identification and characterization of transferase genes of groups B, C2, and E1

1993

Liu, D.; Haase, A.; Lindqvist, L.; Lindberg, A.; Reeves, P.

J. Bacteriol.

175

3408-3413

Links to other databases for dTDP-beta-L-rhamnose

top print hide

Show Links (1 entry)

ChEBI

PubChem