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Ligand 4-hydroxymandelonitrile

Basic Ligand Information

Molecular Structure

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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

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

2.4.1.178

587060

UDP-glucose + 4-hydroxymandelonitrile = UDP + taxiphyllin

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2.4.1.85

723366

UDP-glucose + 4-hydroxymandelonitrile = UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside

-

4.1.2.11

4889, 4896, 4893

4-Hydroxymandelonitrile = ?

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Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Substrate (4 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

2.4.1.178

587060

UDP-glucose + 4-hydroxymandelonitrile = UDP + taxiphyllin

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2.4.1.85

660095, 723366

UDP-glucose + 4-hydroxymandelonitrile = UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside

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4.1.2.11

4889, 4890, 4891, 4896, 4893

4-Hydroxymandelonitrile = ?

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4.1.2.47

704762

p-hydroxymandelonitrile = ?

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Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.14.14.37

-

2-hydroxy(p-hydroxyphenyl)acetaldoxime = 4-hydroxymandelonitrile + H2O

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1.14.14.44

-

4-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + O2 = hydroxy(4-hydroxyphenyl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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1.14.14.44

-

4-hydroxyphenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = hydroxy(4-hydroxyphenyl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O

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1.14.14.44

2 entries

1.14.17.1

438618

4-hydroxybenzyl cyanide + ascorbate + O2 = 4-hydroxymandelonitrile + dehydroascorbate + H2O

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3.2.1.117

-

dhurrin + H2O = D-glucose + 4-hydroxymandelonitrile

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3.2.1.117

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taxiphyllin + H2O = D-glucose + 4-hydroxymandelonitrile

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3.2.1.117

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

possibly an inhibitor, 1 mg/ml bovine serum albumin protects

2.4.1.85

489461

-

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

-

4.1.2.11

0.55

-

4889

-

4.1.2.11

0.7

-

4890, 4891

-

2 entries

References & Links

Literature References (11)

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Show Reference (11 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4889

-

Metabolism of aromatic compounds in higher plants. II. Purification and properties of the oxynitrilase of Sorghum vulgare

1961

Bove, C.; Conn, E.E.

J. Biol. Chem.

236

207-210

4890

5922969

The metabolism of aromatic compounds in higher plants. VII. On the requirement of hydroxynitrile lyase for plants

1966

Seely, M.K.; Criddle, R.S.; Conn, E.E.

J. Biol. Chem.

241

4457-4462

4891

-

Hydroxynitrile lyase (Sorghum vulgare)

1971

Seely, M.K.; Conn, E.E.

Methods Enzymol.

17B

239-244

4893

16661725

Subcellular localization of dhurrin beta-glucosidase and hydroxynitrile lyase in the mesophyll cells of Sorghum leaf blades

1981

Thayer, S.S.; Conn, E.E.

Plant Physiol.

67

617-622

4896

15299660

Crystallographic studies and preliminary X-ray investigation of (S)-p-hydroxy-mandelonitrile lyase from Sorghum bicolor L.

1996

Lauble, H.; Knoedler, S.; Schindelin, H.; Foerster, S.; Wajant, H.; Effenberger, F.

Acta Crystallogr. Sect. D

52

887-889

438618

6693426

Alternate substrates of dopamine beta-hydroxylase. I. Kinetic investigations of benzyl cyanides as substrates and inhibitors

1984

Colombo, G.; Rajashekhar, B.; Giedroc, D.P.; Villafranca, J.J.

J. Biol. Chem.

259

1593-1600

489461

10585420

The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity

1999

Jones, P.R.; Moller, B.L.; Hoj, P.B.

J. Biol. Chem.

274

35483-35491

587060

6230992

Biosynthesis of cyanogenic glucosides: in vitro analysis of the glucosylation step

1984

Hösel, W.; Schiel, O.

Arch. Biochem. Biophys.

229

177-186

660095

12946413

The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor

2003

Hansen, K.S.; Kristensen, C.; Tattersall, D.B.; Jones, P.R.; Olsen, C.E.; Bak, S.; Moller, B.L.

Phytochemistry

64

143-151

704762

19433222

Andexer, J.N.; Sehl, T.; von Langermann, J.; Frindi-Wosch, I.; Rosenkranz, T.; Fitter, J.; Gruber, K.; Kragl, U.; Eggert, T.; Pohl, M.: Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold

2009

Guterl, J.K.

J. Biotechnol.

141

166-173

723366

21620426

Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions

2011

Jensen, K.; Osmani, S.A.; Hamann, T.; Naur, P.; Moller, B.L.

Phytochemistry

72

2113-2123

Links to other databases for 4-hydroxymandelonitrile

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Show Links (1 entry)

ChEBI

PubChem

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