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Ligand (+)-exo-5-hydroxycamphor

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for (+)-exo-5-hydroxycamphor

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (20 results)

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Show Natural Product (20 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

1noo, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

4jx1, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

5wk7, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

6wfl, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

20 entries

Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Substrate (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.327

5-exo-hydroxycamphor + NAD+ = bornane-2,5-dione + NADH + H+

740317

-

1.14.15.1

(+)-exo-5-hydroxycamphor + reduced putidaredoxin + O2 = 5-oxocamphor + oxidized putidaredoxin + H2O

725602

1noo, 3D-view

1.14.15.1

(+)-exo-5-hydroxycamphor + reduced putidaredoxin + O2 = 5-oxocamphor + oxidized putidaredoxin + H2O

725602

4jx1, 3D-view

1.14.15.1

(+)-exo-5-hydroxycamphor + reduced putidaredoxin + O2 = 5-oxocamphor + oxidized putidaredoxin + H2O

725602

5wk7, 3D-view

1.14.15.1

(+)-exo-5-hydroxycamphor + reduced putidaredoxin + O2 = 5-oxocamphor + oxidized putidaredoxin + H2O

725602

6wfl, 3D-view

1.14.15.1

(R)-exo-5-hydroxycamphor + O2 + reduced putidaredoxin = 2,5-diketocamphane + oxidized putidaredoxin + H2O

702799

1noo, 3D-view

1.14.15.1

(R)-exo-5-hydroxycamphor + O2 + reduced putidaredoxin = 2,5-diketocamphane + oxidized putidaredoxin + H2O

702799

4jx1, 3D-view

1.14.15.1

(R)-exo-5-hydroxycamphor + O2 + reduced putidaredoxin = 2,5-diketocamphane + oxidized putidaredoxin + H2O

702799

5wk7, 3D-view

1.14.15.1

(R)-exo-5-hydroxycamphor + O2 + reduced putidaredoxin = 2,5-diketocamphane + oxidized putidaredoxin + H2O

702799

6wfl, 3D-view

1.14.15.1

8 entries

Product in Enzyme-catalyzed Reactions (47 results)

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Show Product (47 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.327

bornane-2,5-dione + NADH + H+ = 5-exo-hydroxycamphor + NAD+

0

-

1.14.13.155

camphor + NADH + H+ + O2 = 5-exo-hydroxycamphor + NAD+ + H2O

0

-

1.14.14.1

(+)-camphor + [reduced NADPH-hemoprotein reductase] + O2 = (+)-exo-5-hydroxycamphor + [oxidized NADPH-hemoprotein reductase] + H2O

0

-

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced ferredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized ferredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + NADH + H+ + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + NADH + H+ + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + NADH + H+ + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + NADH + H+ + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(1R)-(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(1R)-(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(1R)-(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(1R)-(+)-camphor + O2 + reduced putidaredoxin = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(1R)-(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(1R)-(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(1R)-(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(1R)-(+)-camphor + reduced putidaredoxin + O2 = (+)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0, 347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

1noo, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0, 347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

4jx1, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0, 347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

5wk7, 3D-view

1.14.15.1

(+)-camphor + putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0, 347690, 347691, 347692, 347693, 347694, 347695, 347697, 347701, 347702, 347704, 347705, 347706, 347707, 347708, 347710, 347713

6wfl, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + reduced putidaredoxin + O2 = (R)-exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(1R)-camphor + putidaredoxin + O2 = 5-exo-(1R)-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

1noo, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

4jx1, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

5wk7, 3D-view

1.14.15.1

(+)-camphor + O2 + reduced putidaredoxin = exo-5-hydroxycamphor + oxidized putidaredoxin + H2O

0

6wfl, 3D-view

1.14.15.1

DL-camphor + reduced putidaredoxin + NADH + H+ + O2 = exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

1noo, 3D-view

1.14.15.1

DL-camphor + reduced putidaredoxin + NADH + H+ + O2 = exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

4jx1, 3D-view

1.14.15.1

DL-camphor + reduced putidaredoxin + NADH + H+ + O2 = exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

5wk7, 3D-view

1.14.15.1

DL-camphor + reduced putidaredoxin + NADH + H+ + O2 = exo-5-hydroxycamphor + oxidized putidaredoxin + NAD+ + H2O

0

6wfl, 3D-view

1.14.15.1

44 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (24 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (24 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

1noo, 3D-view

1.14.15.1

4jx1, 3D-view

1.14.15.1

5wk7, 3D-view

1.14.15.1

6wfl, 3D-view

1.14.15.1

24 entries

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

1.1.1.327

0.0279

-

pH 8.0, 45°C

740317

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

347690

4378858

Mixed function oxidation. IV. An induced methylene hydroxylase in camphor oxidation

1965

Hedegaard, J.; Gunsalus, I.C.

J. Biol. Chem.

240

4038-4043

347691

4341491

The role of putidaredoxin and P450 cam in methylene hydroxylation

1972

Tyson, C.T.; Lipscomb, J.D.; Gunsalus, I.C.

J. Biol. Chem.

247

5777-5784

347692

672627

Bacterial P-450cam methylene monooxygenase components: cytochrome m, putidaredoxin, and putidaredoxin reductase

1978

Gunsalus, I.C.; Wagner, G.C.

Methods Enzymol.

52

166-188

347693

7240237

Interaction of 5-bromocamphor with cytochrome P-450 cam. Production of 5-ketocamphor from a mixed spin state hemoprotein

1981

Gould, P.V.; Gelb, M.H.; Sligar, S.G.

J. Biol. Chem.

256

6686-6691

347694

7073732

Cytochrome P450cam catalyzed epoxidation of dehydrocamphor

1982

Gelb, M.H.; Mälkönen, P.; Sligar, S.G.

Biochem. Biophys. Res. Commun.

104

853-858

347695

6501299

Novel reactivity of cytochrome P-450-CAM. Methyl hydroxylation of 5,5-difluorocamphor

1984

Smith Eble, K.; Dawson, J.H.

J. Biol. Chem.

259

14389-14393

347697

7074020

Stereochemistry and deuterium isotope effects in camphor hydroxylation by the cytochrome P450cam monoxygenase system

1982

Gelb, M.H.; Heimbrook, D.C.; Mälkönen, P.; Sligar, S.G.

Biochemistry

21

370-377

347701

11051559

Roles of the axial push effect in cytochrome P450cam studied with the site-directed mutagenesis at the heme proximal site

2000

Yoshioka, S.; Takahashi, S.; Ishimori, K.; Morishima, I.

J. Inorg. Biochem.

81

141-151

347702

8475046

Engineering cytochrome P-450cam to increase the stereospecificity and coupling of aliphatic hydroxylation

1993

Loida, P.J.; Sligar, S.G.

Protein Eng.

6

207-212

347704

10698731

The catalytic pathway of cytochrome P450cam at atomic resolution

2000

Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A.M.; Maves, S.A.; Benson, D.E.; Sweet, R.M.; Ringe, D.; Petsko, G.A.; Sligar, S.G.

Science

287

1615-1622

347705

11706033

Complex formation of cytochrome P450cam with putidaredoxin: evidence for protein-specific interactions involving the proximal thiolate ligand

2002

Unno, M.; Christian, J.F.; Sjodin, T.; Benson, D.E.; Macdonald, I.D.G.; Sligar, S.G.; Champion, P.M.

J. Biol. Chem.

277

2547-2553

347706

9542996

The dimerization of Pseudomonas putida cytochrome P450cam: practical consequences and engineering of a monomeric enzyme

1997

Nickerson, D.P.; Wong, L.L.

Protein Eng.

10

1357-1361

347707

11583152

Benign synthesis of 2-ethylhexanoic acid by cytochrome P450cam: enzymatic, crystallographic, and theoretical studies

2001

French, K.J.; Strickler, M.D.; Rock, D.A.; Rock, D.A.; Bennett, G.A.; Wahlstrom, J.L.; Goldstein, B.M.; Jones, J.P.

Biochemistry

40

9532-9538

347708

11231299

Oxidation of polychlorinated benzenes by genetically engineered CYP101 (cytochrome P450(cam))

2001

Jones, J.P.; O'Hare, E.J.; Wong, L.L.

Eur. J. Biochem.

268

1460-1467

347710

11168358

Proximal cysteine residue is essential for the enzymatic activities of cytochrome P450cam

2001

Yoshioka, S.; Takahashi, S.; Hori, H.; Ishimori, K.; Morishima, I.

Eur. J. Biochem.

268

252-259

347713

10371217

Surface-modified mutants of cytochrome p450cam enzymatic properties and electrochemistry

1999

Lo, K.K.; Wong, L.L.; Hill, A.O.

FEBS Lett.

451

342-346

702799

18098319

P450cam biocatalysis in surfactant-stabilized two-phase emulsions

2008

Ryan, J.; Clark, D.

Biotechnol. Bioeng.

99

1311-1319

725602

21562741

Identification of camphor oxidation and reduction products in Pseudomonas putida: new activity of the cytochrome P450cam system

2011

Prasad, B.; Rojubally, A.; Plettner, E.

J. Chem. Ecol.

37

657-667

740317

-

Biocatalytic synthesis of a diketobornane as a building block for bifunctional camphor derivatives

2013

Hofer, M.; Strittmatter, H.; Sieber, V.

ChemCatChem

5

3351-3357

Links to other databases for (+)-exo-5-hydroxycamphor

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Show Links (1 entry)

ChEBI

PubChem