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Ligand 4a-hydroxytetrahydrobiopterin

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 4a-hydroxytetrahydrobiopterin

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.96

(6R)-6-(L-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin = (6R)-6-(L-erythro-1,2-dihydroxypropyl)-7,8-dihydro-6H-pterin + H2O

742313

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In Vivo Product in Enzyme-catalyzed Reactions (11 results)

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Show Natural Product (11 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.16.1

L-phenylalanine + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

phenylalanine + tetrahydrobiopterin + O2 = tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

L-tyrosine + tetrahydrobiopterin + O2 = 3,4-dihydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

L-tyrosine + tetrahydrobiopterin + O2 = L-dopa + 4a-hydroxytetrahydrobiopterin

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1.14.16.4

L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.4

L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

6 entries

1.14.16.2

2 entries

1.14.16.4

2 entries

1.14.16.7

L-phenylalanine + tetrahydrobiopterin + O2 = 3-hydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin

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Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.96

(6R)-6-(L-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin = (6R)-6-(L-erythro-1,2-dihydroxypropyl)-7,8-dihydro-6H-pterin + H2O

742313, 690623

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4.2.1.96

4a-hydroxy-tetrahydrobiopterin = 7,8-dihydrobiopterin + H2O

5930, 5937

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4.2.1.96

4a-hydroxytetrahydrobiopterin = ?

5936

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4.2.1.96

3 entries

Product in Enzyme-catalyzed Reactions (21 results)

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Show Product (21 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.16.1

L-phenylalanine + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxy-tetrahydrobiopterin

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1.14.16.1

L-phenylalanine + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + (7R)-5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + (7R,S)-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 5,6,7,8-tetrahydro-L-biopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 5,6,7,8-tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + 6,7-dimethyl-5,6,7,8-tetrahydropterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-phenylalanine + tetrahydrobiopterin + O2 = L-tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-tryptophan + 5,6,7,8-tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxytryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

phenylalanine + tetrahydrobiopterin + O2 = tyrosine + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

L-tyrosine + 5,6,7,8-tetrahydrobiopterin + O2 = 3,4-dihydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

L-tyrosine + tetrahydrobiopterin + O2 = 3,4-dihydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

L-tyrosine + tetrahydrobiopterin + O2 = L-dopa + 4a-hydroxytetrahydrobiopterin

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1.14.16.2

tyramine + tetrahydrobiopterin + O2 = dopamine + 4a-hydroxytetrahydrobiopterin

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1.14.16.4

L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.4

L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.4

L-tryptophan + tetrahydrobiopterin = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin

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1.14.16.1

13 entries

1.14.16.2

4 entries

1.14.16.4

3 entries

1.14.16.7

L-phenylalanine + tetrahydrobiopterin + O2 = 3-hydroxy-L-phenylalanine + 4a-hydroxytetrahydrobiopterin

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Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.2.1.96

23

-

N61D

690623

4.2.1.96

23

-

N61D/Q45R/K98Q

690623

4.2.1.96

23

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Q45R/K98Q

690623

4.2.1.96

24

-

wild-type

690623

4.2.1.96

4 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

4.2.1.96

0.004

-

wild-type

690623

4.2.1.96

0.0044

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Q45R/K98Q

690623

4.2.1.96

0.0047

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mutant enzyme C82R

5936

4.2.1.96

0.0052

-

N61D

690623

4.2.1.96

0.0052

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wild type enzyme

5936

4.2.1.96

0.0053

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N61D/Q45R/K98Q

690623

4.2.1.96

6 entries

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

5930

-

Human liver pterin 4alpha-carbinolamine dehydratase. Purification and characterization

1992

Rebrin, I.; Petruschka, L.; Curtius, H.Ch.; Adler, C.; Herrmann, F.H.

Pteridines

3

55-57

5936

8618906

Characterization of the wild-type form of 4a-carbinolamine dehydratase and two naturally occuring mutants associated with hyperphenylalaninemia

1995

Johen, G.; Kowlessur, D.; Citron, B.A.; Kaufman, S.

Proc. Natl. Acad. Sci. USA

92

12384-12388

5937

1465414

Identity of 4a-carbinolamine dehydratase, a component of the phenylalanine hydroxylation system, and DCoH, a transregulator of homeodomain proteins

1992

Citron, B.A.; Davis, M.D.; Milstien, S.; Gutierrez, J.; Mendel, D.B.; Crabtree, G.R.; Kaufman, S.

Proc. Natl. Acad. Sci. USA

89

11891-11894

690623

18644344

Determinants of oligomerization of the bifunctional protein DCoHalpha and the effect on its enzymatic and transcriptional coactivator activities

2008

Hevel, J.M.; Pande, P.; Viera-Oveson, S.; Sudweeks, T.J.; Jaffree, L.S.; Hansen, C.M.; Ayling, J.E.

Arch. Biochem. Biophys.

477

356-362

742313

25899859

Molecular and enzymatic characterization of two enzymes BmPCD and BmDHPR involving in the regeneration pathway of tetrahydrobiopterin from the silkworm Bombyx mori

2015

Li, W.; Gong, M.; Shu, R.; Li, X.; Gao, J.; Meng, Y.

Comp. Biochem. Physiol. B

186

20-27

Links to other databases for 4a-hydroxytetrahydrobiopterin

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Show Links (1 entry)

ChEBI

PubChem

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