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Basic Ligand Information
Roles as Enzyme Ligand
Enzyme Kinetic Parameters
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Ligand Renilla luciferin

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Basic Ligand Information

Molecular Structure

Picture of Renilla luciferin (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₂₆H₂₁N₃O₂

Renilla luciferin

KAEGGIFPLJZUOZ-UHFFFAOYSA-N

Synonyms:

2,8-dibenzyl-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one, b-coelenterazine, benzylluciferin, coelenterazine-h, coelenterazine h, h-coelenterazine

Pathway Source

Pathways

MetaCyc

coral bioluminescence

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Roles as Enzyme Ligand

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

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.5

coelenterazine h + O2 = excited coelenteramide h monoanion + CO2

745436, 765705, 764866

1.13.12.5

Renilla luciferin + O2 = oxidized Renilla luciferin + CO2 + hv

439333, 439334, 439335, 439336

1.13.12.5

2 entries

2.8.2.10

3'-phosphoadenylyl sulfate + Renilla luciferin = adenosine 3',5'-bisphosphate + luciferyl sulfate

760508, 762107, 737724

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.2.10

Renilla luciferyl sulfate + adenosine 3',5'-bisphosphate = Renilla luciferin + 3'-phosphoadenylylsulfate

643816, 643817

Substrate in Enzyme-catalyzed Reactions (16 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.13

h-coelenterazine + O2 = ? + CO2 + hv

744220

1.13.12.13

h-coelenterazine + O2 = oxidized h-coelenterazine + CO2 + hn

728741

1.13.12.13

h-coelenterazine + O2 = oxidized h-coelenterazine + CO2 + hnu

689868, 726882

1.13.12.24

h-coelenterazine + O2 = h-coelenteramide + CO2 + hnu

744892

1.13.12.24

[apoaequorin] + h-coelenterazine + O2 + 3 Ca2+ = [excited state blue fluorescent protein] + CO2

744216

1.13.12.5

2,8-dibenzyl-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one + O2 = oxidized 2,8-dibenzyl-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one + CO2 + hn

656822

1.13.12.5

b-coelenterazine + O2 = ?

700904

1.13.12.5

benzylluciferin + O2 = oxidized benzylluciferin + CO2 + hv

439336

1.13.12.5

coelenterazine h + O2 = coelenteramide h + CO2 + hv

745096, 746365

1.13.12.5

coelenterazine h + O2 = excited coelenteramide h monoanion + CO2

745436, 765705, 764866

1.13.12.5

coelenterazine-H + O2 = ?

728746, 701005

1.13.12.5

coelenterazine-h + O2 = coelenteramide h + CO2 + hv

745436

1.13.12.5

h-coelenterazine + O2 = ?

728741

1.13.12.5

h-coelenterazine + O2 = hnu + ?

695982

1.13.12.5

Renilla luciferin + O2 = oxidized Renilla luciferin + CO2 + hv

439333, 439334, 439335, 439336, 439337, 439338, 671287

3'-phosphoadenylyl sulfate + Renilla luciferin = adenosine 3',5'-bisphosphate + luciferyl sulfate

760508, 762107, 737724

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.2.10

Renilla luciferyl sulfate + adenosine 3',5'-bisphosphate = Renilla luciferin + 3'-phosphoadenylylsulfate

643816, 643817

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.13

764497

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.13.12.5

1.85

439336

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

1.13.12.5

0.0039

pH 7.8, 25°C, recombinant His-tagged enzyme

745096

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.12.13

0.101

pH and temperature not specified in the publication

764497

References & Links

Literature References (29)

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Show Reference (29 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

439333

4154104

Bioluminescence in coelenterates

1974

Cormier, M.J.; Hori, K.; Anderson, J.M.

Biochim. Biophys. Acta

346

137-164

439334

12797

Purification and properties of Renilla reniformis luciferase

1977

Matthews, J.C.; Hori, K.; Cormier, M.J.

Biochemistry

85-91

439335

4397765

Mechanism of oxidative carbon dioxide production during Renilla reniformis bioluminescence

1971

DeLuca, M.; Dempsey, M.E.; Hori, K.; Wampler, J.E.; Cormier, M.J.

Proc. Natl. Acad. Sci. USA

1658-1660

439336

36127

Renilla reniformis bioluminescence: luciferase-catalyzed production of nonradiating excited states from luciferin analogues and elucidation of the excited state species involved in energy transfer to Renilla green fluorescent protein

1979

Hart, R.C.; Matthews, J.C.; Hori, K.; Cormier, M.J.

Biochemistry

2204-2210

439337

21679

Substrate and substrate analogue binding properties of Renilla luciferase

1977

Matthews, J.C.; Hori, K.; Cormier, M.J.

Biochemistry

5217-5220

439338

4395343

Isolation and properties of Renilla reniformis luciferase, a low molecular weight energy conversion enzyme

1971

Karkhanis, Y.D.; Cormier, M.J.

Biochemistry

317-326

643816

4392153

Studies on the bioluminescence of Renilla reniformis. VII. Conversion of luciferin into luciferyl sulfate by luciferin sulfokinase

1970

Cormier, M.J.; Hori, K.; Karkhanis, Y.D.

Biochemistry

1184-1189

643817

A bioluminescence assay for PAP(3',5'-diphosphoadenosine) and PAPS (3'-phosphoadenylyl sulfate)

1978

Anderson, J.M.; Hori, K.; Cormier, M.J.

Methods Enzymol.

244-257

656822

15142411

Characterization of coelenterazine analogs for measurements of Renilla luciferase activity in live cells and living animals

2004

Zhao, H.; Doyle, T.C.; Wong, R.J.; Cao, Y.; Stevenson, D.K.; Piwnica-Worms, D.; Contag, C.H.

Mol. Imaging

43-54

671287

10860516

A noncommercial dual luciferase enzyme assay system for reporter gene analysis

2000

Dyer, B.W.; Ferrer, F.A.; Klinedinst, D.K.; Rodriguez, R.

Anal. Biochem.

282

158-161

689868

17900925

Overexpression, purification and characterization of the catalytic component of Oplophorus luciferase in the deep-sea shrimp, Oplophorus gracilirostris

2007

Inouye, S.; Sasaki, S.

Protein Expr. Purif.

261-268

695982

17981153

Identification of two catalytic domains in a luciferase secreted by the copepod Gaussia princeps

2008

Inouye, S.; Sahara, Y.

Biochem. Biophys. Res. Commun.

365

96-101

700904

19461967

The cAMP-dependent protein kinase inhibitor H-89 attenuates the bioluminescence signal produced by renilla luciferase

2009

Herbst, K.J.; Allen, M.D.; Zhang, J.

Plos One

e5642

701005

19208811

Mechanism of PTC124 activity in cell-based luciferase assay of nonsense codon suppression

2009

Auld, D.S.; Thorne, N.; Maguire, W.F.; Inglese, J.

Proc. Natl. Acad. Sci. USA

106

3585-3590

726882

23792095

C6-Deoxy coelenterazine analogues as an efficient substrate for glow luminescence reaction of nanoKAZ: the mutated catalytic 19 kDa component of Oplophorus luciferase

2013

Inouye, S.; Sato, J.; Sahara-Miura, Y.; Yoshida, S.; Kurakata, H.; Hosoya, T.

Biochem. Biophys. Res. Commun.

437

23-28

728741

23274053

Expression, purification and luminescence properties of coelenterazine-utilizing luciferases from Renilla, Oplophorus and Gaussia: comparison of substrate specificity for C2-modified coelenterazines

2013

Inouye, S.; Sahara-Miura, Y.; Sato, J.; Iimori, R.; Yoshida, S.; Hosoya, T.

Protein Expr. Purif.

150-156

728746

23973867

Novel functional Renilla luciferase mutant provides long-term serum stability and high luminescence activity

2013

Song, W.C.; Sung, H.J.; Park, K.S.; Choi, J.W.; Cho, J.Y.; Um, S.H.

Protein Expr. Purif.

215-220

737724

27227579

Sulfoluciferin is biosynthesized by a specialized luciferin sulfotransferase in fireflies

2016

Fallon, T.R.; Li, F.S.; Vicent, M.A.; Weng, J.K.

Biochemistry

3341-3344

744216

17254548

Imidazole-assisted catalysis of luminescence reaction in blue fluorescent protein from the photoprotein aequorin

2007

Inouye, S.; Sasaki, S.

Biochem. Biophys. Res. Commun.

354

650-655

744220

24491536

Luminescence enhancement of the catalytic 19 kDa protein (KAZ) of Oplophorus luciferase by three amino acid substitutions

2014

Inouye, S.; Sato, J.; Sahara-Miura, Y.; Yoshida, S.; Hosoya, T.

Biochem. Biophys. Res. Commun.

445

157-162

744892

16545379

Blue fluorescent protein from the calcium-sensitive photoprotein aequorin catalytic properties for the oxidation of coelenterazine as an oxygenase

2006

Inouye, S.; Sasaki, S.

FEBS Lett.

580

1977-1982

745096

27651278

Probing the emitter site of Renilla luciferase using small organic molecules; an attempt to understand the molecular architecture of the emitter site

2016

Salehi, F.; Emamzadeh, R.; Nazari, M.; Rasa, S.M.

Int. J. Biol. Macromol.

1253-1260

745436

28796298

New Insights into the Molecular characteristics behind the function of Renilla luciferase

2018

Kahrani, Z.F.; Ganjalikhany, M.R.; Rasa, S.M.M.; Emamzadeh, R.

J. Cell. Biochem.

119

1780-1790

746365

27881682

Stabilization of luciferase from Renilla reniformis using random mutations

2017

Shigehisa, M.; Amaba, N.; Arai, S.; Higashi, C.; Kawanabe, R.; Matsunaga, A.; Laksmi, F.A.; Tokunaga, M.; Ishibashi, M.

Protein Eng. Des. Sel.

7-13

760508

32736692

Efficient conversion to Cypridina luciferin from Cypridina luciferyl sulfate, coupled with enzymatic sulfation of acetic acid

2020

Nakamura, M.; Matsuda, K.; Morikawa, T.; Ishizuka, K.; Inouye, S.

Biochem. Biophys. Res. Commun.

529

678-684

762107

31230356

Enzymatic conversion of Cypridina luciferyl sulfate to Cypridina luciferin with coenzyme A as a sulfate acceptor in Cypridina (Vargula) hilgendorfii

2019

Nakamura, M.; Matsuda, K.; Nakamura, M.; Yamashita, K.; Suzuki, T.; Inouye, S.

Photochem. Photobiol.

1376-1386

764497

31765054

Bioluminescence profiling of nanoKAZ/nanoLuc luciferase using a chemical library of coelenterazine analogues

2020

Coutant, E.P.; Gagnot, G.; Hervin, V.; Baatallah, R.; Goyard, S.; Jacob, Y.; Rose, T.; Janin, Y.L.

Chemistry

948-958

764866

29800661

Kinetics, structure, and dynamics of Renilla luciferase solvated in binary mixtures of glycerol and water and the mechanism by which glycerol obstructs the enzyme emitter site

2018

Khoshnevisan, G.; Emamzadeh, R.; Nazari, M.; Rasa, S.M.M.; Sariri, R.; Hassani, L.

Int. J. Biol. Macromol.

117

617-624

765705

29288731

Expression and characterization of the Renilla luciferase with the cumulative mutation

2018

Ishibashi, M.; Kawanabe, R.; Amaba, N.; Arai, S.; Laksmi, F.; Komori, K.; Tokunaga, M.

Protein Expr. Purif.

145