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Ligand hydrazine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.18.6.1

hydrazine + reduced ferredoxin = 2 NH3 + oxidized ferredoxin

742740

-

1.7.2.7

hydrazine + H2O + ferricytochrome c = nitric oxide + ammonium + ferrocytochrome c

737496, 738539, 739162, 739169, 738118, 739753, 738120

-

1.7.2.8

hydrazine + 4 ferricytochrome c = N2 + 4 ferrocytochrome c

763819, 763841, 765764

-

1.7.2.8

hydrazine + ferricytochrome c = N2 + ferrocytochrome c

738539, 739162, 736020, 738690

-

1.7.2.8

2 entries

1.7.2.9

hydrazine + ferricytochrome c = ? + ferrocytochrome c + H+

763248

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.18.6.1

N2 + 4 reduced ferredoxin = hydrazine + 4 oxidized ferredoxin

0

-

1.7.2.7

nitric oxide + ammonium + 3 ferrocytochrome c = hydrazine + H2O + 3 ferricytochrome c

0

-

1.7.2.7

nitric oxide + ammonium + 3 H+ = hydrazine + H2O

0

-

3.5.1.4

acetohydrazide + H2O = hydrazine + acetate

209122

-

3.5.1.4

propionohydrazide + H2O = hydrazine + propionate

209122

-

1.7.2.7

2 entries

3.5.1.4

2 entries

Substrate in Enzyme-catalyzed Reactions (30 results)

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Show Substrate (30 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.18.6.1

hydrazine + ? = ?

728683, 659426

-

1.18.6.1

hydrazine + reduced ferredoxin = 2 NH3 + oxidized ferredoxin

742740

-

1.18.6.1

N2H4 + ? = ?

658483

-

1.7.2.6

hydrazine + ferricytochrome c = ? + ferrocytochrome c

639387

-

1.7.2.6

hydrazine + O2 = N2 + H2O

657930

-

1.7.2.6

hydrazine + phenazine methosulfate = N2 + reduced phenazine methosulfate

394326

-

1.18.6.1

3 entries

1.7.2.6

3 entries

1.7.2.7

hydrazine + H2O + ferricytochrome c = nitric oxide + ammonium + ferrocytochrome c

737496, 738539, 739162, 739169, 738118, 739753, 738120

-

1.7.2.8

hydrazine + 2,6-dichloroindophenol = ? + reduced 2,6-dichloroindophenol

695734

-

1.7.2.8

hydrazine + 2,6-dichlorophenolindophenol = N2 + reduced 2,6-dichlorophenolindophenol

394344

-

1.7.2.8

hydrazine + 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide = ? + reduced methylthiazolyltetrazolium bromide

699041

-

1.7.2.8

hydrazine + 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide = N2 + reduced 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide

724029

-

1.7.2.8

hydrazine + 4 bovine heart ferricytochrome c = N2 + 4 bovine heart ferrocytochrome c

764303

-

1.7.2.8

hydrazine + 4 ferricytochrome c = N2 + 4 ferrocytochrome c

763819, 763841, 765764

-

1.7.2.8

hydrazine + ferricyanide = ? + ferrocyanide

695734

-

1.7.2.8

hydrazine + ferricyanide = N2 + ferrocyanide

394344

-

1.7.2.8

hydrazine + ferricytochrome = N2 + ferrocytochrome

394344

-

1.7.2.8

hydrazine + ferricytochrome c = ? + ferrocytochrome c

695734

-

1.7.2.8

hydrazine + ferricytochrome c = N2 + ferrocytochrome c

738539, 739162, 736020, 738690

-

1.7.2.8

hydrazine + methylthiazolyltetrazolium bromide = ? + reduced methylthiazolyltetrazolium bromide

695734

-

1.7.2.8

hydrazine + methylthiazolyltetrazolium bromide = N2 + reduced methylthiazolyltetrazolium bromide

394344

-

1.7.2.8

hydrazine + NH3 + 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide = ?

699041

-

1.7.2.8

hydrazine + NH3 + phenazine methosulfate = ?

699041

-

1.7.2.8

hydrazine + phenazine methosulfate = ? + reduced phenazine methosulfate

695734

-

1.7.2.8

16 entries

1.7.2.9

hydrazine + ferricytochrome c = ? + ferrocytochrome c + H+

763248

-

3.5.1.4

short-chain amides + hydrazine = acid hydrazides + NH3

655819

-

4.3.1.1

hydrazine + fumarate = 2-hydrazinosuccinic acid

691802

-

4.3.1.2

mesaconate + hydrazine = ?

729057

-

6.3.4.2

ATP + UTP + NH2NH2 = ADP + phosphate + ?

649003

-

6.3.4.2

ATP + UTP + NH2NH2 = ADP + phosphate + CTP + N4-amino CTP

661644

-

6.3.4.2

2 entries

6.3.5.5

2 ATP + hydrazine + HCO3- = 2 ADP + phosphate + N-amino carbamoyl phosphate

652028

-

Product in Enzyme-catalyzed Reactions (18 results)

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Show Product (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.18.6.1

N2 + 4 reduced ferredoxin = hydrazine + 4 oxidized ferredoxin

0

-

1.7.2.7

nitric oxide + ammonium + 3 ferrocytochrome c = hydrazine + H2O + 3 ferricytochrome c

0

-

1.7.2.7

nitric oxide + ammonium + 3 H+ = hydrazine + H2O

0

-

1.7.2.7

2 entries

2.3.2.2

L-glutamylhydrazine + methylamine = gamma-L-glutamylmethylamide + hydrazine

0

-

2.3.2.9

(gamma-L-glutamyl)hydrazine + H2O = L-glutamate + hydrazine

488026

-

3.4.11.1

L-leucinhydrazide + H2O = L-leucine + H2NNH2

0

-

3.5.1.11

phenylacetic hydrazide + H2O = phenylacetate + hydrazine

0

-

3.5.1.4

acetohydrazide + H2O = hydrazine + acetate

209122

-

3.5.1.4

propionohydrazide + H2O = hydrazine + propionate

209122

-

3.5.3.6

Nomega-amino-Arg + H2O = L-citrulline + hydrazine

0

-

3.5.3.6

Nomega-amino-L-arginine + H2O = hydrazine + L-citrulline

0

-

3.5.3.6

Nomega-amino-L-arginine + H2O = L-citrulline + hydrazine

0

-

4.3.1.2

(2S)-2-hydrazinosuccinic acid = fumarate + hydrazine

6061

-

4.3.1.2

2-hydrazino-3-chlorosuccinic acid = chlorofumarate + hydrazine

6061

-

4.3.1.2

2-hydrazino-3-ethylsuccinic acid = ethylfumarate + hydrazine

6061

-

4.3.1.2

2-hydrazino-3-isopropylsuccinic acid = isopropylfumarate + hydrazine

6061

-

4.3.1.2

2-hydrazino-3-propylsuccinic acid = propylfumarate + hydrazine

6061

-

4.3.1.2

hydrazino-3-methylsuccinic acid = mesaconate + hydrazine

6061

-

3.5.1.4

2 entries

3.5.3.6

3 entries

4.3.1.2

6 entries

Inhibitor in Enzyme-catalyzed Reactions (56 results)

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Show Inhibitors (56 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.129

inhibitory at 100 mM

285825

-

1.1.3.13

1 mM, complete inhibition

688123

-

1.1.3.13

89% residual activity at 1 mM

740872

-

1.1.3.4

-

696865

-

1.1.3.4

partial

389806

-

1.1.3.13

2 entries

1.1.3.4

2 entries

1.1.3.9

1 mM, 41% inhibition

687852

-

1.1.99.14

77% residual activity at 1 mM

725738

-

1.1.99.20

-

389904

-

1.1.99.20

weak

389908

-

1.1.99.20

2 entries

1.11.1.7

5 mM, 45% residual activity

743176

-

1.11.1.B2

uncompetitive; uncompetitive inhibition, inhibition constant: 0.3 mM

659641

-

1.11.1.B8

-

672311

-

1.17.1.9

-

288115

-

1.18.6.1

and derivatives

440158

-

1.2.1.12

-

725568

-

1.2.1.23

1-3 mM

288146

-

1.2.1.49

1-3 mM

288146

-

1.2.1.9

protonated and neutral form, compete with the attacking water molecule for the binding site E268, inhibition mechanism

288346

-

1.2.3.1

1 mM, 28% residual activity

699045

-

1.4.2.1

-

391704

-

1.4.3.2

46% residual activity at 1 mM (pH 5.5)

725575

-

1.4.3.2

93% residual activity at 1 mM

742930

-

1.4.3.2

2 entries

1.4.3.21

complete inhibition at 1 mM

742933

-

1.4.3.22

10 mM, 95% inhibition

656323

-

1.4.3.8

-

391965, 391966, 391967

-

1.4.9.1

-

396585

-

1.4.9.2

-

396592

-

1.4.9.2

complete inhibition at 0.1 mM

655062

-

1.4.9.2

2 entries

1.7.1.10

1 mM, complete inhibition

394439

-

1.7.2.6

50% inhibition at 0.1 mM

394326

-

1.7.2.6

-

719635

-

1.7.2.6

2 entries

1.7.2.8

competes strongly with hydroxylamine. Addition of 0.015 mM, 0.035 mM, and 0.35 mM results in 15%, 50%, and 85% inhibition, respectively

394344

-

1.7.99.1

competitive inhibition

394261

-

1.7.99.1

hydrazine sulfate inhibits 10-15% at 4 mM

394269

-

1.7.99.1

hydroxylamine reductase 2, slight

394264

-

1.7.99.1

3 entries

2.1.2.1

-

441401

-

2.5.1.49

-

637830

-

2.5.1.61

-

489923

-

2.6.1.19

-

637035, 637056, 637059

-

2.6.1.42

-

640013, 640020

-

2.7.1.35

0.00055 mM, 50% inhibition

641404

-

2.7.1.35

0.05 mM, 50% inhibition

641404

-

2.7.1.35

2 entries

2.7.7.41

-

643297

-

3.1.1.11

-

750823

-

3.1.6.8

-

135554, 135683

-

3.4.11.9

inactivates wild-type hcAMPP and R535A mutant enzymes

755161

-

3.4.21.50

-

36618

-

3.5.1.1

-

208942

-

4.1.1.57

-

4720

-

4.2.1.84

1 mM

648437

-

4.3.1.10

25 mM, complete inhibition

6031

-

4.3.1.19

-

210846

-

4.4.1.4

-

34630

-

5.1.1.8

-

2156

-

5.3.99.7

1 mM, 82% inhibition

648825

-

5.4.3.3

-

3397, 3402

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

1.7.3.4

4n4l, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.7.2.8

1.7

-

at pH 7.0 and 35°C

764303

1.7.2.8

3

6

at pH 7.0 and 37°C

738690

1.7.2.8

2 entries

1.7.2.9

4.9

-

37°C, pH not specified in the publication

763248

4.3.1.1

92

-

reverse reaction, 750 mM hydrazine, at pH 8, 22°C in 50 mM phosphate

691802

4.3.1.1

94

-

reverse reaction, 20 mM fumarate, at pH 8, 22°C in 50 mM phosphate

691802

4.3.1.1

2 entries

K_M Value (10 results)

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Show KM Value (10 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.7.2.6

0.003

-

pH 7.5, 25°C, with enzyme form HAO-A, that forms only the monocyano derivative of heme P460

639387

1.7.2.6

0.005

-

pH 7.5, 25°C, with enzyme form HAO-B, that forms a mono- and dicyano complex

639387

1.7.2.8

0.0055

-

pH 8.0, 35°C

695734

1.7.2.8

0.0076

-

at pH 7.0 and 35°C

764303

1.7.2.8

0.01

-

at pH 7.0 and 37°C

738690

1.7.2.8

0.018

-

pH 8.0, 35°C, reduction of methylthiazolyltetrazolium bromide via phenazine methosulfate

394344

1.7.2.8

0.025

-

pH 8.0, 35°C

699041

1.7.2.6

2 entries

1.7.2.8

5 entries

1.7.2.9

0.054

-

37°C, pH not specified in the publication

763248

4.3.1.1

1.54

-

reverse reaction, 750 mM hydrazine, at pH 8, 22°C in 50 mM phosphate

691802

4.3.1.1

308

-

reverse reaction, 20 mM fumarate, at pH 8, 22°C in 50 mM phosphate

691802

4.3.1.1

2 entries

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.11.1.B2

0.35

-

-

659641

1.2.1.9

6.3

-

wild-type enzyme

288346

1.2.1.9

109

-

mutant E268A

288346

1.2.1.9

254

-

mutant E268Q

288346

1.2.1.9

3 entries

References & Links

Literature References (93)

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Show Reference (93 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2156

14189888

Purification and properties of inducible hydroxyproline 2-epimerase from Pseudomonas

1964

Adams, E.; Norton, I.L.

J. Biol. Chem.

239

1525-1535

3397

4540127

Purification and properties of beta-lysine mutase, a pyridoxal phosphate and B12 coenzyme dependent enzyme

1973

Baker, J.J.; van der Drift, C.; Stadtman, T.C.

Biochemistry

12

1054-1063

3402

5011967

The role of pyridoxal phosphate in the B12-coenzyme-dependent D-alpha-lysine mutase reaction

1972

Morley, C.G.D.; Stadtman, T.C.

Biochemistry

11

600-605

4720

-

Amino acid metabolism in microorganisms. Part IV. L-Methionine decarboxylase produced by a Streptomyces strain

1968

Hagino, H.; Nakayama, K.

Agric. Biol. Chem.

32

727-733

6031

-

L-Serine O-sulphate lyase, a new enzyme in extracts from higher plants

1977

Murakoshi, I.; Sanda, A.; Haginiwa, J.

Chem. Pharm. Bull.

25

1829-1832

6061

-

Preparation of N-substituted aspartic acids via enantiospecific conjugate addition of N-nucleophiles to fumaric acids using methylaspartase: synthetic utility and mechanistic implications

1997

Gulzar, M.S.; Akhtar, M.; Gani, D.

J. Chem. Soc. Perkin Trans. I

1197

649-655

34630

-

S-Alkyl-L-cysteine sulfoxide lyase [Allium cepa (onion)]

1971

Schwimmer, S.

Methods Enzymol.

17B

475-478

36618

7845202

Lysyl endopeptidase of Achromobacter lyticus

1994

Sakiyama, F.; Masaki, T.

Methods Enzymol.

244

126-137

135554

-

Arylsulfatases

1971

Nicholls, R.G.; Roy, A.B.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

5

21-41

135683

40545

Isolation, characterization and the role of rabbit testicular arysulphatase A in fertilization

1979

Farooqui, A.A.; Srivastava, P.N.

Biochem. J.

181

331-337

208942

16345199

Purification and some biological properties of asparaginase from Azotobacter vinelandii

1977

Gaffar, S.A.; Shetna, Y.I.

Appl. Environ. Microbiol.

33

508-514

209122

110350

Kinetic mechanismen of the aliphatic amidase from Pseudomonas aeruginosa

1979

Woods, M.J.; Findlater, J.D.; Orsi, B.A.

Biochim. Biophys. Acta

567

225-237

210846

-

Comparative characterization of L-threonine dehydratase in seven species of unicellular marine algae

1972

Desai, I.D.; Laub, D.; Anita, N.J.

Phytochemistry

11

277-287

285825

14154441

L-threonic acid dehydrogenase: Purification and properties

1964

Aspen, A.J.; Jakoby, W.B.

J. Biol. Chem.

239

710-713

288115

4301624

Formate dehydrogenase from the pea seedling

1968

Kanamori, T.; Suzuki, Y.

Enzymologia

35

185-197

288146

4383524

alpha-Keto aldehyde dehydrogenase, an enzyme that catalyzes the enzymic oxidation of methylglyoxal to pyruvate

1967

Monder, C.

J. Biol. Chem.

242

4603-4609

288346

11722561

Engineered nonphosphorylating gylceraldehyde 3-phosphate dehydrogenase at position 268 binds hydroxylamine and hydrazine as acyl acceptors

2001

Marchal, S.; Branlant, G.

Eur. J. Biochem.

268

5764-5770

389806

-

Glucose oxidase

1963

Bentley, R.

The Enzymes, 2nd Ed. (Boyer, P. D. , Lardy, H. , Myrbäck, K. , eds. )

7

567-586

389904

-

Identification of the prosthetic group and further characterization of a novel enzyme, polyethylne glycol dehydrogenase

1985

Kawai, F.; Yamanaka, H.; Ameyama, M.; Shinagawa, E.; Matsushita, K.; Adachi, O.

Agric. Biol. Chem.

49

1071-1076

389908

-

Purification and characterization of constitutive polyethylene glycol (PEG) dehydrogenase of a PEG 4000-utilizing Flavobacterium sp. No. 203

1989

Yamanaka, H.; Kawai, F.

J. Ferment. Bioeng.

67

324-330

391704

5016640

Glycine-cytochrome c reductase from Nitrobacter agilis

1972

Sanders, H.K.; Becker, G.E.; Nason, A.

J. Biol. Chem.

247

2015-2025

391965

-

Ethanolamine oxidase

1966

Narrod, S.A.; Jakoby, W.B.

Methods Enzymol.

8

354-357

391966

14209947

Metabolism of ethanolamine, an ethanoloxidase

1964

Narrod, S.A.; Jakoby, W.B.

J. Biol. Chem.

239

2189-2193

391967

4709585

Ethanolamine oxidase from the blowfly, Phormia regina (Diptera: Insecta)

1973

Kulkarni, A.P.; Hodgson, E.

Comp. Biochem. Physiol. B

44

407-422

394261

13782715

Hydroxylamine reductase from Pseudomonas aeruginosa

1961

Walker, G.C.; Nicholas, D.J.D.

Biochim. Biophys. Acta

49

361-368

394264

5420040

Possible active sites in nitrite reductase and hydroxylamine reductases from vegetable marrow (Curcubita pepo L.)

1970

Hucklesby, D.P.; Hewitt, E.J.; James, D.M.

Biochem. J.

117

30P

394269

14342247

The reduction of nitrate, nitrite and hydroxylamine to ammonia by enzymes from Curcubita pepo L. in the presence of reduced benzyl viologen as electron donor

1965

Cresswell, C.F.; Hageman, R.H.; Hewitt, E.J.; Hucklesby, D.P.

Biochem. J.

94

40-53

394326

199251

Hydroxylamine oxidoreductase of Nitrosomonas. Oxidation of diethyldithiocarbamate concomitant with stimulation of nitrite synthesis

1977

Hooper, A.B.; Terry, K.R.; Maxwell, P.C.

Biochim. Biophys. Acta

462

141-152

394344

10820012

Involvement of a novel hydroxylamine oxidoreductase in anaerobic ammonium oxidation

2000

Schalk, J.; de Vries, S.; Kuenen, J.G.; Jetten, M.S.

Biochemistry

39

5405-5412

394439

13744035

Pyridine nucleotide-nitrite and -hydroxylamine enzymes from soybean leaves

1960

Roussos, G.G.; Nason, A.

J. Biol. Chem.

235

2997-3007

396585

10346915

Biochemical and electrochemical characterization of quinohemoprotein amine dehydrogenase from Paracoccus denitrificans

1999

Takagi, K.; Torimura, M.; Kawaguchi, K.; Kano, K.; Ikeda, T.

Biochemistry

38

6935-6942

396592

8188594

Aromatic amine dehydrogenase, a second tryptophan tryptophylquinone enzyme

1994

Govindaraj, S.; Eisenstein, E.; Jones, L.H.; Sanders-Loehr, J.; Chistoserdov, A.Y.; Davidson, V.L.; Edwards, S.L.

J. Bacteriol.

176

2922-2929

440158

4670204

Nitrogenase complex and its components

1972

Bulen, W.A.; LeComte, J.R.

Methods Enzymol.

24B

456-470

441401

5808700

Purification and properties of serine hydroxymethylase from soluble and mitochondrial fractions of rabbit liver

1969

Fujioka, M.

Biochim. Biophys. Acta

185

338-349

488026

14209959

Studies on the gamma-glutamyltransferase of Agaricus bisporus

1964

Gigliotti, H.J.; Levenberg, B.

J. Biol. Chem.

239

2274-2284

489923

4542566

Polypyrroles formed from porphobilinogen and amines by uroporphyrinogen synthetase of Rhodopseudomonas spheroides

1973

Davies, R.C.; Neuberger, A.

Biochem. J.

133

471-492

637035

4156051

Subunit structure and kinetic properties of 4-aminobutyrate-2-ketoglutarate transaminase purified from mouse brain

1974

Schousboe, A.; Wu, J.Y.; Roberts, E.

J. Neurochem.

23

1189-1195

637056

7362249

gamma-Aminobutyrate:alpha-ketoglutarate aminotransferase from Pseudomonas sp. F-126: purification, crystallization, and enzymologic properties

1980

Yonaha, K.; Toyama, S.

Arch. Biochem. Biophys.

200

156-164

637059

3917915

4-Aminobutyrate:2-oxoglutarate aminotransferase of Streptomyces griseus: purification and properties

1985

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