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Ligand divinyl chlorophyllide a

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

KEGG

Biosynthesis of secondary metabolites, Porphyrin metabolism

MetaCyc

3,8-divinyl-chlorophyllide a biosynthesis I (aerobic, light-dependent), 3,8-divinyl-chlorophyllide a biosynthesis II (anaerobic), 3,8-divinyl-chlorophyllide a biosynthesis III (aerobic, light independent), bacteriochlorophyll a biosynthesis, bacteriochlorophyll b biosynthesis, bacteriochlorophyll c biosynthesis, bacteriochlorophyll d biosynthesis, bacteriochlorophyll e biosynthesis, chlorophyll a biosynthesis I, chlorophyll a biosynthesis II, chlorophyll a biosynthesis III, chlorophyll a2 biosynthesis, chlorophyll b2 biosynthesis more

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Natural Substrate (10 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = 3-monovinyl chlorophyllide a + NADP+

739277

-

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = 3-vinyl-chlorophyllide a + NADP+

746105

-

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

746037, 745221, 762685, 763382, 762912

-

1.3.1.75

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster

746260

-

1.3.1.75

8-vinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

762912

-

1.3.1.75

C8-vinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

744270

-

1.3.7.13

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster

746037

-

1.3.7.13

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + NADPH + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster + NADP+

744270

-

1.3.1.75

6 entries

1.3.7.13

2 entries

1.3.7.14

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + ATP + H2O + H+ = bacteriochlorophyllide g + oxidized ferredoxin [iron-sulfur] cluster + ADP + phosphate

739649

-

1.3.7.15

8-vinyl chlorophyllide a + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = chlorophyllide a + 2 oxidized ferredoxin [iron-sulfur] cluster

762912, 763382, 763435

-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.33

divinyl protochlorophyllide a + NADPH = divinyl chlorophyllide a + NADP+

0

-

1.3.1.75

chlorophyllide a + NADP+ = divinyl chlorophyllide a + NADPH + H+

0

-

1.3.7.13

chlorophyllide a + 2 oxidized ferredoxin [iron-sulfur] cluster = 8-vinyl chlorophyllide a + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+

0

-

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = 3-monovinyl chlorophyllide a + NADP+

726217, 739277

-

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = 3-vinyl-chlorophyllide a + NADP+

746105

-

1.3.1.75

3,8-divinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

746037, 745221, 762685, 762912, 763382

-

1.3.1.75

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster

746260

-

1.3.1.75

8-vinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

762912

-

1.3.1.75

C8-vinyl chlorophyllide a + NADPH + H+ = chlorophyllide a + NADP+

744270

-

1.3.1.75

divinyl chlorophyllide a + NADPH + H+ = monovinyl chlorophyllide a + NADP+

726217

-

1.3.7.13

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster

746037

-

1.3.7.13

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + NADPH + H+ = chlorophyllide a + oxidized ferredoxin [iron-sulfur] cluster + NADP+

744270

-

1.3.1.75

7 entries

1.3.7.13

2 entries

1.3.7.14

3,8-divinyl chlorophyllide a + reduced ferredoxin [iron-sulfur] cluster + ATP + H2O + H+ = bacteriochlorophyllide g + oxidized ferredoxin [iron-sulfur] cluster + ADP + phosphate

739649

-

1.3.7.15

8-vinyl chlorophyllide a + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = chlorophyllide a + 2 oxidized ferredoxin [iron-sulfur] cluster

762912, 763382, 763435

-

3.1.1.100

3,8-divinyl-chlorophyllide a + H2O = 3,8-divinyl-bacteriochlorophyllide d + methanol + CO2

751810

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.33

divinyl protochlorophyllide a + NADPH = divinyl chlorophyllide a + NADP+

0

-

1.3.1.75

chlorophyllide a + NADP+ = divinyl chlorophyllide a + NADPH + H+

0

-

1.3.7.13

chlorophyllide a + 2 oxidized ferredoxin [iron-sulfur] cluster = 8-vinyl chlorophyllide a + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+

0

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.7.15

inhibitory effect of 8 V-Chlide on 3 V-BChlide production inhibitory effect of 8 V-Chlide on the C7=C8 reduction of COR

762912

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (7 results)

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Show Turnover Number (7 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.3.1.75

0.0071

-

pH 8.0, 22°C, recombinant Strep II-tagged dimeric enzyme, low salt condition

763382

1.3.1.75

0.0074

-

pH 8.0, 22°C, recombinant Strep II-tagged dimeric enzyme, high salt condition

763382

1.3.1.75

0.66

-

pH 8.0, 22°C, recombinant Strep II-tagged oligomeric enzyme, low salt condition

763382

1.3.1.75

0.66

-

recombinant BciA, pH and temperature not specified in the publication

762912

1.3.1.75

0.66

-

pH and temperature not specified in the publication

762912

1.3.7.15

0.00027

-

recombinant enzyme BchX/BchY, pH and temperature not specified in the publication

762912

1.3.7.15

0.011

-

pH 8.0, 22°C, recombinant BchYZ heterodimer

763382

1.3.1.75

5 entries

1.3.7.15

2 entries

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.75

0.023

-

pH 8.0, 22°C, recombinant Strep II-tagged oligomeric enzyme, low salt condition

763382

1.3.1.75

0.032

-

pH 8.0, 22°C, recombinant Strep II-tagged dimeric enzyme, low salt condition

763382

1.3.1.75

0.035

-

pH 8.0, 22°C, recombinant Strep II-tagged dimeric enzyme, high salt condition

763382

1.3.1.75

0.23

-

pH and temperature not specified in the publication

762912

1.3.7.15

0.0014

-

recombinant enzyme BchX/BchY, pH and temperature not specified in the publication

762912

1.3.7.15

0.0059

-

pH 8.0, 22°C, recombinant BchYZ heterodimer

763382

1.3.1.75

4 entries

1.3.7.15

2 entries

References & Links

Literature References (13)

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Show Reference (13 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

726217

20484022

Divinyl chlorophyll(ide) a can be converted to monovinyl chlorophyll(ide) a by a divinyl reductase in rice

2010

Wang, P.; Gao, J.; Wan, C.; Zhang, F.; Xu, Z.; Huang, X.; Sun, X.; Deng, X.

Plant Physiol.

153

994-1003

739277

17991629

The major route for chlorophyll synthesis includes [3,8-divinyl]-chlorophyllide a reduction in Arabidopsis thaliana

2007

Nagata, N.; Tanaka, R.; Tanaka, A.

Plant Cell Physiol.

48

1803-1808

739649

23386973

An unexpectedly branched biosynthetic pathway for bacteriochlorophyll b capable of absorbing near-infrared light

2013

Tsukatani, Y.; Yamamoto, H.; Harada, J.; Yoshitomi, T.; Nomata, J.; Kasahara, M.; Mizoguchi, T.; Fujita, Y.; Tamiaki, H.

Sci. Rep.

3

1217

744270

24942864

Elucidation of the preferred routes of C8-vinyl reduction in chlorophyll and bacteriochlorophyll biosynthesis

2014

Canniffe, D.P.; Chidgey, J.W.; Hunter, C.N.

Biochem. J.

462

433-440

745221

26903415

Two unrelated 8-vinyl reductases ensure production of mature chlorophylls in Acaryochloris marina

2016

Chen, G.E.; Hitchcock, A.; Jackson, P.J.; Chaudhuri, R.R.; Dickman, M.J.; Hunter, C.N.; Canniffe, D.P.

J. Bacteriol.

198

1393-1400

746037

24399236

Evolution of a new chlorophyll metabolic pathway driven by the dynamic changes in enzyme promiscuous activity

2014

Ito, H.; Tanaka, A.

Plant Cell Physiol.

55

593-603

746105

23154534

One divinyl reductase reduces the 8-vinyl groups in various intermediates of chlorophyll biosynthesis in a given higher plant species, but the isozyme differs between species

2013

Wang, P.; Wan, C.; Xu, Z.; Wang, P.; Wang, W.; Sun, C.; Ma, X.; Xiao, Y.; Zhu, J.; Gao, X.; Deng, X.

Plant Physiol.

161

521-534

746260

24586995

A tale of two reductases extending the bacteriochlorophyll biosynthetic pathway in E. coli

2014

Tikh, I.B.; Quin, M.B.; Schmidt-Dannert, C.

PLoS ONE

9

e89734

751810

30182280

In vitro demethoxycarbonylation of various chlorophyll analogs by a BciC enzyme

2018

Teramura, M.; Harada, J.; Tamiaki, H.

Photosynth. Res.

139

163-171

762685

33956163

Distribution and functional analysis of the two types of 8-vinyl reductase involved in chlorophyll biosynthesis in marine cyanobacteria

2021

Suehiro, H.; Tanaka, R.; Ito, H.

Arch. Microbiol.

203

3565-3575

762912

32180325

Chlorophyllide a oxidoreductase preferentially catalyzes 8-vinyl reduction over B-ring reduction of 8-vinyl chlorophyllide a in the late steps of bacteriochlorophyll biosynthesis

2020

Yamamoto, H.; Mizoguchi, T.; Tsukatani, Y.; Tamiaki, H.; Kurisu, G.; Fujita, Y.

ChemBioChem

21

1760-1766

763382

-

Rapid C8-vinyl reduction of divinyl-chlorophyllide a by BciA from Rhodobacter capsulatus

2018

Azai, C.; Kobayashi, M.; Mizoguchi, T.; Tamiaki, H.; Terauchi, K.; Tsukatani, Y.

J. Photochem. Photobiol. A

353

661-666

763435

30317478

Expression, purification, and activity analysis of chlorophyllide oxidoreductase and Ni2+-sirohydrochlorin a,c-diamide reductase

2019

Moser, J.; Jasper, J.; Ramos, J.; Sowa, S.; Layer, G.

Methods Mol. Biol.

1876

125-140

Links to other databases for divinyl chlorophyllide a

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Show Links (1 entry)

ChEBI

PubChem

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