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Ligand 2-C-methyl-D-erythritol 2,4-cyclodiphosphate

Basic Ligand Information

Molecular Structure

Related pathways

Show all BRENDA pathways known for 2-C-methyl-D-erythritol 2,4-cyclodiphosphate

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Roles as Enzyme Ligand

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

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.7.1

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized ferredoxin

674441, 673638, 676579, 766376

4G9P, 3D-view

1.17.7.1

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized ferredoxin

674441, 673638, 676579, 766376

4S38, 3D-view

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced flavodoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized flavodoxin

766487, 767428

-

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced flavodoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized flavodoxin

675579, 728960, 639344, 745426, 745692

-

1.17.7.1

2 entries

1.17.7.3

2 entries

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

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.7.1

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced ferredoxin

-

4G9P, 3D-view

1.17.7.1

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced ferredoxin

-

4S38, 3D-view

1.17.7.1

2 entries

1.17.7.3

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized flavodoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced flavodoxin

-

-

4.6.1.12

2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP

-

1H48, 3D-view

4.6.1.12

2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol = 2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP

-

1H48, 3D-view

4.6.1.12

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.7.1

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized ferredoxin

674441, 673638, 676579, 766376

4G9P, 3D-view

1.17.7.1

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized ferredoxin

674441, 673638, 676579, 766376

4S38, 3D-view

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced flavodoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + 2 oxidized flavodoxin

766487, 767428

-

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced 10-methyl-5-deazaisoalloxazine = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized 10-methyl-5-deazaisoalloxazine

639344

-

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced deazaflavin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized deazaflavin

675579

-

1.17.7.3

2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced flavodoxin = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized flavodoxin

675579, 728960, 639344, 729725, 745426, 745692

-

1.17.7.1

2 entries

1.17.7.3

4 entries

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.7.1

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced ferredoxin

-

4G9P, 3D-view

1.17.7.1

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced ferredoxin

-

4S38, 3D-view

1.17.7.1

2 entries

1.17.7.3

(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H2O + oxidized flavodoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + reduced flavodoxin

-

-

4.6.1.12

2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + CMP

-

1H48, 3D-view

4.6.1.12

2-phospho-4-(cytidine 5'-diphospho)-2C-methyl-D-erythritol = 2C-methyl-D-erythritol-2,4-cyclodiphosphate + CMP

-

1H48, 3D-view

4.6.1.12

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (7 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (7 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.17.7.1

4G9P, 3D-view

1.17.7.1

4S38, 3D-view

1.17.7.1

4G9P, 3D-view

1.17.7.1

4S38, 3D-view

1.17.7.1

4G9P, 3D-view

1.17.7.1

4S38, 3D-view

1.17.7.1

6 entries

4.6.1.12

1H48, 3D-view

Enzyme Kinetic Parameters

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.17.7.3

0.7

-

pH 8.0, 37°C, photometric assay

675579

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

639344

12571359

The deoxyxylulose phosphate pathway of isoprenoid biosynthesis: Studies on the mechanisms of the reactions catalyzed by IspG and isph protein

2003

Rohdich, F.; Zepeck, F.; Adam, P.; Hecht, S.; Kaiser, J.; Laupitz, R.; Grawert, T.; Amslinger, S.; Eisenreich, W.; Bacher, A.; Arigoni, D.

Proc. Natl. Acad. Sci. USA

100

1586-1591

673638

16480720

Isoprenoid biosynthesis in plant chloroplasts via the MEP pathway: direct thylakoid/ferredoxin-dependent photoreduction of GcpE/IspG

2006

Seemann, M.; Tse Sum Bui, B.; Wolff, M.; Miginiac-Maslow, M.; Rohmer, M.

FEBS Lett.

580

1547-1552

674441

15792953

Cyanobacterial non-mevalonate pathway: (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase interacts with ferredoxin in Thermosynechococcus elongatus BP-1

2005

Okada, K.; Hase, T.

J. Biol. Chem.

280

20672-20679

675579

16268586

Biosynthesis of isoprenoids. Purification and properties of IspG protein from Escherichia coli

2005

Zepeck, F.; Graewert, T.; Kaiser, J.; Schramek, N.; Eisenreich, W.; Bacher, A.; Rohdich, F.

J. Org. Chem.

70

9168-9174

676579

15863698

The Arabidopsis IspH homolog is involved in the plastid nonmevalonate pathway of isoprenoid biosynthesis

2005

Hsieh, M.H.; Goodman, H.M.

Plant Physiol.

138

641-653

728960

12434382

Isoprenoid biosynthesis through the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE) is a [4Fe-4S] protein

2002

Seemann, M.; Tse Sum Bui, B.; Wolff, M.; Tritsch, D.; Campos, N.; Boronat, A.; Marquet, A.; Rohmer, M.

Angew. Chem. Int. Ed. Engl.

41

4337-4339

729725

15978585

fldA is an essential gene required in the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis

2005

Puan, K.; Wang, H.; Dairi, T.; Kuzuyama, T.; Morita, C.

FEBS Lett.

579

3802-3806

745426

28279816

Enhanced performance of the methylerythritol phosphate pathway by manipulation of redox reactions relevant to IspC, IspG, and IspH

2017

Zhou, J.; Yang, L.; Wang, C.; Choi, E.; Kim, S.

J. Biotechnol.

248

1-8

745426

28279816

Enhanced performance of the methylerythritol phosphate pathway by manipulation of redox reactions relevant to IspC, IspG, and IspH

2017

Zhou, J.; Yang, L.; Wang, C.; Choi, E.; Kim, S.

J. Biotechnol.

248

1-8

745426

2 entries

745692

28864262

Balanced activation of IspG and IspH to eliminate MEP intermediate accumulation and improve isoprenoids production in Escherichia coli

2017

Li, Q.; Fan, F.; Gao, X.; Yang, C.; Bi, C.; Tang, J.; Liu, T.; Zhang, X.

Metab. Eng.

44

13-21

766376

35272619

De novo assembly and analysis of Polygonatum cyrtonema Hua and identification of genes involved in polysaccharide and saponin biosynthesis

2022

Li, D.; Wang, Q.; Chen, S.; Liu, H.; Pan, K.; Li, J.; Luo, C.; Wang, H.

BMC Genomics

23

195

766487

35285984

Irreversible inhibition of IspG, a target for the development of new antimicrobials, by a 2-vinyl analogue of its MEcPP substrate

2022

Herrscher, V.; Witjaksono, C.; Buchotte, M.; Ferret, C.; Massicot, F.; Vasse, J.L.; Borel, F.; Behr, J.B.; Seemann, M.

Chemistry

28

e202200241

767428

31690314

Investigation of the methylerythritol 4-phosphate pathway for microbial terpenoid production through metabolic control analysis

2019

Volke, D.C.; Rohwer, J.; Fischer, R.; Jennewein, S.

Microb. Cell Fact.

18

192

Links to other databases for 2-C-methyl-D-erythritol 2,4-cyclodiphosphate

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Show Links (1 entry)