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Ligand L-cystine

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for L-cystine

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Natural Substrate (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.8.1.6

L-cystine + NADH + H+ = 2 L-cysteine + NAD+

743682

-

1.8.1.6

NADH + L-cystine = ?

440354

-

1.8.1.6

2 entries

1.8.4.4

cystine + GSH = cysteine + GSSG

395017, 395018, 395019, 395014, 395015, 395016

-

4.4.1.1

L-cystine + H2O = pyruvate + NH3 + L-thiocysteine

721432

-

4.4.1.35

L-cystine + H2O = L-thiocysteine + pyruvate + NH3

741128

-

4.4.1.35

L-cystine = L-thiocysteine + 2-aminoprop-2-enoate

741128

-

4.4.1.35

2 entries

4.4.1.8

L-cystine + H2O = ? + NH3

747857

-

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein TcyA](side 1) = ADP + phosphate + L-cystine(side 2) + [cystine-binding protein TcyA](side 1)

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein](side 1) = ADP + phosphate + L-cystine(side 2) + [cystine-binding protein](side 1)

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein][side 1] = ADP + phosphate + L-cystine[side 2] + [cystine-binding protein][side 1]

-

-

7.4.2.12

3 entries

Substrate in Enzyme-catalyzed Reactions (40 results)

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Show Substrate (40 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.2

L-cystine + H2O + O2 = 2-oxo-3-mercaptopropanoic acid + NH3 + H2O2

391775, 651026

-

1.4.3.2

L-cystine + H2O + O2 = ?

724190

-

1.4.3.2

L-cystine + H2O + O2 = ? + NH3 + H2O2

391773, 651026, 661038

-

1.8.1.6

L-cystine + glutathione = L-cysteine + GSSG

667725

-

1.8.1.6

L-cystine + NADH + H+ = 2 L-cysteine + NAD+

743682

-

1.8.1.6

NADH + L-cystine + H+ = NAD+ + L-cysteine

673491

-

1.8.1.6

NADH + L-cystine = ?

440354

-

1.8.1.6

NADH + L-cystine = NAD+ + L-cysteine

440353, 440355, 440356, 440354

-

1.4.3.2

3 entries

1.8.1.6

5 entries

1.8.1.9

cystine + NADPH + H+ = 2 cysteine + NADP+

742565

-

1.8.4.4

cystine + GSH = cysteine + GSSG

395017, 395018, 395019, 395014, 395015, 395016

-

1.8.4.4

L-cystine + GSH = L-cysteine + GSSG

395014

-

1.8.4.4

2 entries

1.8.4.9

cystine + glutathione = cysteine + glutathione disulfide

660399

-

2.3.2.2

5-L-glutamyl-4-nitroanilide + L-cystine = 4-nitroaniline + 5-L-glutamyl-L-cystine

487944, 487902, 487932, 487914, 487931, 487936, 487950, 487929, 487930, 487903

-

2.6.1.64

L-cystine + phenylpyruvate = cystine ketimine + phenylalanine

640176

-

2.8.1.7

L-cystine + Slr0077 = pyruvate + Slr0077-SSH

660879

-

2.8.1.7

L-cystine = ?

645621

-

2.8.1.7

2 entries

3.5.99.7

L-cystine + H2O = ?

735145

-

4.1.99.2

L-cystine + H2O = ? + pyruvate + NH3

33454

-

4.3.1.10

L-cystine = ?

6035

-

4.4.1.1

L-cystine + H2O = 2 NH3 + 2 pyruvate + 2 hydrogen sulfide

653162

-

4.4.1.1

L-cystine + H2O = L-thiocysteine + pyruvate + NH3

707582, 709005

-

4.4.1.1

L-cystine + H2O = NH3 + ?

652626, 651351

-

4.4.1.1

L-cystine + H2O = NH3 + pyruvate + L-thiocysteine

692897, 690396

-

4.4.1.1

L-cystine + H2O = pyruvate + NH3 + L-thiocysteine

721432

-

4.4.1.1

L-cystine + H2O = thiocysteine + pyruvate + NH3

34499

-

4.4.1.1

L-cystine = ?

5584, 586904

-

4.4.1.1

7 entries

4.4.1.11

L-cystine + H2O = ?

701789

-

4.4.1.13

L-cystine + H2O = ?

713846

-

4.4.1.13

L-cystine + H2O = L-thiocysteine + pyruvate + NH3

34708, 34686, 34690, 34698, 652362, 651551, 34712, 34713, 674725, 34688, 34715, 34691, 34689

-

4.4.1.13

L-cystine + H2O = pyruvate + NH3 + L-thiocysteine

664205

-

4.4.1.13

L-cystine = ?

34678

-

4.4.1.13

4 entries

4.4.1.2

L-cystine + H2O = ?

722937

-

4.4.1.28

L-cystine + H2O = ?

748127

-

4.4.1.35

L-cystine + H2O = L-thiocysteine + pyruvate + NH3

741128, 652362, 651551

-

4.4.1.35

L-cystine = L-thiocysteine + 2-aminoprop-2-enoate

741128

-

4.4.1.4

cystine = ?

657029

-

4.4.1.4

L-cystine = ?

34617, 34609

-

4.4.1.4

L-cystine = pyruvate + NH4+ + S2- + L-cysteine

676740

-

4.4.1.35

2 entries

4.4.1.4

3 entries

4.4.1.8

L-cystine + H2O = ? + NH3

747857

-

6.3.2.5

ATP + (R)-4'-phosphopantothenate + cystine = (R)-4'-phosphopantothenoyl-L-cystine + ADP + phosphate

4406

-

Product in Enzyme-catalyzed Reactions (20 results)

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Show Product (20 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.99.52

L-cysteine + O2 = L-cystine + H2O

-

-

1.14.99.55

starch + cysteine + O2 = malto-oligosaccharide aldonic acid + cystine + H2O

-

-

1.8.1.9

L-cysteine + NADPH = L-cystine + NADP+

-

-

1.8.3.2

cysteine + O2 = cystine + H2O2

-

-

1.8.3.2

2 L-Cys + O2 = L-cystine + H2O2

-

-

1.8.3.3

2 L-Cys + O2 = L-cystine + H2O2

-

-

1.8.3.3

L-cysteine + O2 = L-cystine

-

-

1.8.3.2

2 entries

1.8.3.3

2 entries

1.8.4.1

cysteine + homocystine = cystine + 2 homocysteine

-

-

1.8.4.2

L-cysteine + protein disulfide = cystine + protein-dithiol

-

-

3.4.11.10

L-cystinyl-p-nitroanilide + H2O = L-cystine + p-nitroaniline

-

-

3.4.11.22

Cystinyl 4-nitroanilide + H2O = Cystine + 4-nitroaniline

28290

-

3.4.11.3

L-cystine-di-beta-naphthylamide + 2 H2O = L-cystine + 2 beta-naphthylamine

-

-

3.4.11.3

L-cystine-di-p-nitroanilide + H2O = L-cystine + p-nitroaniline

-

-

3.4.11.3

2 entries

3.5.2.9

L-2-iminothiazolidine-4-carboxylate + H2O = L-cystine

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein Ngo0372](side 1) = ADP + phosphate + L-cystine(side 2) + [cystine-binding protein Ngo0372](side 1)

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein TcyA](side 1) = ADP + phosphate + L-cystine(side 2) + [cystine-binding protein TcyA](side 1)

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein](side 1) = ADP + phosphate + L-cystine(side 2) + [cystine-binding protein](side 1)

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein II][side 1] = ADP + phosphate + L-cystine[side 2] + [cystine-binding protein II][side 1]

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein I][side 1] = ADP + phosphate + L-cystine[side 2] + [cystine-binding protein I][side 1]

-

-

7.4.2.12

ATP + H2O + L-cystine-[cystine-binding protein][side 1] = ADP + phosphate + L-cystine[side 2] + [cystine-binding protein][side 1]

-

-

7.4.2.12

6 entries

Activator in Enzyme-catalyzed Reactions (7 results)

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Show Activating Compound (7 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.16

-

285441

-

2.1.1.5

-

673003

-

2.3.2.7

20 mM, slight activation

488009

-

3.5.1.1

causes an increase in Vmax value and a decrease in Km value, nonessential mode of activation

719379

-

3.5.5.1

16% activation at 1 mM

209746

-

4.2.2.10

5 mM, 142% of initial activity

729668

-

4.2.2.2

25% activation at 1 mM, 73% activation at 5 mM

666570

-

Inhibitor in Enzyme-catalyzed Reactions (29 results)

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Show Inhibitors (29 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.19

25% residual activity at 2 mM

742674

-

1.12.98.4

-

437770

-

1.13.11.20

42% inhibition at 5 mM

439546

-

1.13.11.5

inhibition not reversed by glutathione

439382

-

1.2.1.11

complete inhibition at 0.01 mM, binds via the cysteine moiety covalently to the catalytic Cys135 of the enzyme, pH-dependent process, optimal at pH 7.0-7.5, inhibition is reversible by DTT, dithioerythritol, 2-mercaptoethanol, dimercaptopropanol, and reduced glutathione, no protection by aspartate-beta-semialdehyde, NADP+ or NADPH, inhibition mechanism and kinetics

654891

-

1.2.1.11

inactivation, reversible by addition of DTT or 2-mercaptoethanol

657298

-

1.2.1.11

2 entries

1.21.3.1

81% inhibition at 1.5 mM

440316

-

1.4.1.4

strongly and selectively inhibits the reductive amination reaction

743643

-

2.1.1.5

-

441233

-

2.1.1.9

55% inhibition at 10 mM

441594

-

2.1.4.2

-

485984

-

2.3.1.30

allosteric inhibition

486773

-

2.5.1.47

competitive versus O-acetyl-L-serine, the cystine-binding residues are highly conserved in all OASS proteins; competitive versus O-acetyl-L-serine, the cystine-binding residues are highly conserved in all OASS proteins. Active site of CysK2–cystine binding structure, overview. Cystine occupies the substrate/product binding site of the enzyme

737756

-

2.7.1.19

oxidized form, inhibition almost completely reversible by addition of reduced dithiothreitol

662126

-

2.7.1.40

2.5 mM, significant inhibition

674052

-

2.7.1.40

inhibits by two different mechanisms, one through the competition with ADP and phosphoenolpyruvate, and the other non-competitively, probable through oxidation of the thiol groups of the enzyme. GSH and cysteamine fully prevent and reverse the inhibition caused by cystine

661404

-

2.7.3.2

cystine inhibited the enzyme activity in a dose- and time-dependent manner and cysteamine prevents and reverses the inhibition caused by cystine, suggesting that cystine inhibits creatine kinase activity by oxidation of the sulfhydryl groups of the enzyme; dose- and time-dependent inhibition, cysteamine prevents and reverses this inhibition

671632

-

2.7.3.2

inhibits creatine kinase activity possibly by oxidation of the sulfhydryl groups of the enzyme. Considering that creatine kinase like other thiol-containing enzymes, is crucial for energy homeostasis and antioxidant defenses, the enzymes inhibition caused by cystine released from lysosomes could be one of the mechanisms of tissue damage in patients with cystinosis

688814

-

2.7.1.40

2 entries

2.7.3.2

2 entries

2.7.4.3

adenylate kinase activity is diminished in the brain cortex of rats loaded with cystine dimethylester (0.0016 mg/g body weight), co-administration with cysteamine (0.00046 mg/g body weight) prevents inhibition of adenylate kinase caused by cystine

705503

-

3.1.1.79

inhibits the enzyme activity in presence of TNF-alpha

714794

-

3.1.3.17

-

94688

-

3.1.4.1

slight inhibition

134132

-

3.2.1.15

-

730876

-

3.5.1.92

5 mM, 15 min, 100% residual activity in absence of substrate S-pantetheine-3-pyruvate, 32% residual activity in presence of the substrate S-pantetheine-3-pyruvate

658224

-

4.1.1.20

-

4110, 4115

-

6.2.1.5

-

805

-

6.3.2.3

1 mM, 11% inhibition

661674

-

6.4.1.1

-

1776

-

7.1.1.3

-

743301

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.8.1.6

30.3

-

pH 7.5, 22°C, wild-type enzyme TRP14

743682

4.4.1.28

29

-

pH 8.3, 30°C

748127

K_M Value (27 results)

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Show KM Value (27 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.4.3.2

5

-

-

391775

1.8.1.6

0.0008

-

pH 7.5, 22°C, wild-type enzyme TRP14

743682

1.8.1.6

0.11

-

-

440354

1.8.1.6

0.9

-

-

440356

1.8.1.6

3 entries

1.8.4.4

0.23

-

-

395019

2.3.2.2

0.029

0.035

D-Glu-4-nitroanilide

487931

2.3.2.2

0.029

0.035

glutathione

487944

2.3.2.2

0.029

0.035

hydrolase reaction

487944, 487931

2.3.2.2

0.029

0.035

kidney enzyme

487930

2.3.2.2

4 entries

2.6.1.64

1.4

-

pH 9.0, 37°C

640176

4.3.1.10

2

-

enzyme A

6035

4.4.1.1

0.032

-

-

34499

4.4.1.1

0.909

-

-

586904

4.4.1.1

1.29

-

pH 8.0, 37°C

653162

4.4.1.13

0.0812

-

-

651551

4.4.1.13

0.25

-

-

34686, 34690

4.4.1.13

0.8

-

-

34688

4.4.1.13

1

-

estimated from steady-state measurements

674725

4.4.1.13

2.32

-

-

652362

4.4.1.13

5.4

-

-

34698

4.4.1.1

3 entries

4.4.1.13

6 entries

4.4.1.28

2.1

-

pH 8.3, 30°C

748127

4.4.1.35

0.0812

-

pH 8.4, 30°C

651551

4.4.1.35

2.32

-

pH 7.6, 22°C

652362

4.4.1.4

1.94

-

homogenous alliinase prepared from fresh garlic cloves

676740

4.4.1.4

2.2

-

alliinase I

657029

4.4.1.4

2.65

-

preparation obtained from garlic powder, activity calculated from the amount of enzymatically formed pyruvate

676740

4.4.1.4

9.7

-

alliinase II

657029

4.4.1.35

2 entries

4.4.1.4

4 entries

References & Links

Literature References (111)

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Show Reference (111 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

805

5166363

Porphyrin biosynthesis in soybean callus tissue system. VIII. Isolation, purification and general properties of succinyl CoA synthetase

1971

Wider, E.A.; Tigier, H.A.

Enzymologia

41

217-231

1776

5047709

Pyruvate carboxylase: inactivation by sulfhydryl group reagents in the presence of certain inorganic anions, substrates, and modifiers and the effects on the allosteric properties of the enzyme

1972

Palacian, E.; Neet, K.E.

Biochim. Biophys. Acta

276

297-312

4110

-

Diaminopimelate decarboxylase (Escherichia coli)

1971

White, P.J.

Methods Enzymol.

17B

140-145

4115

-

Purification and properties of meso-alpha,epsilon-diaminopimelate decarboxylase from Bacillus sphaericus

1981

Asada, Y.; Tanizawa, K.; Kawabata, Y.; Misuno, H.; Soda, K.

Agric. Biol. Chem.

45

1513-1514

4406

13630913

The metabolism of pantothenic acid

1959

Brown, G.M.

J. Biol. Chem.

234

370-378

5584

6364702

The beta-replacement-specific pyridoxal-P-dependent lyases

1984

Braunstein, A.E.; Goryachenkova, E.V.

Adv. Enzymol. Relat. Areas Mol. Biol.

56

1-89

6035

1260040

Substrate specificity of the L-serine O-sulphate degrading activities of Pseudomonas FR

1976

Tudball, N.; O'Neill, J.G.

Biochim. Biophys. Acta

429

616-623

28290

8482390

Purification and characterization of the cystinyl bond cleaving yeast aminopeptidase yscXVI

1993

Tisljar, U.; Wolf, D.H.

FEBS Lett.

322

191-196

33454

-

Elimination, replacement and isomerization reactions by intact cells containing tyrosine phenol lyase

1972

Enei, H.; Matsui, H.; Okumura, S.; Yamada, H.

Agric. Biol. Chem.

36

1869-1876

34499

14209951

Purification and properties of the cystathionine gamma-cleavage enzyme of Neurospora

1964

Flavin, M.; Segal, A.

J. Biol. Chem.

239

2220-2227

34609

-

Aliinase-like enzymes in fruiting bodies of Lentinus edodes: their purification and substrate specificity

1980

Iwami, K.; Yasumoto, K.

Agric. Biol. Chem.

44

3003-3004

34617

-

Enzymatic cleavage of cysteine sulfoxide in Lentinus edodes

1975

Iwami, K.; Yasumoto, K.; Mitsuda, H.

Agric. Biol. Chem.

39

1947-1955

34678

241329

Purification and properties of S-alkyl-L-cysteine lyase from seedlings of Acacia farnesiana Willd.

1975

Mazelis, M.; Creveling, R.K.

Biochem. J.

147

485-491

34686

2821350

Cystathionine beta-lyase from Escherichia coli

1987

Uren, J.R.

Methods Enzymol.

143

483-486

34688

-

beta-Cystathionase (Salmonella)

1971

Guggenheim, S.

Methods Enzymol.

17B

439-442

34689

16535166

Purification and characterization of cystathionine beta-lyase from Lactococcus lactis subsp. cremonis B78 and its possible role in flavor development in cheese

1995

Alting, A.C.; Engels, W.J.M.; van Schalkwijk, S.; Exterkate, F.A.

Appl. Environ. Microbiol.

61

4037-4042

34690

7049234

Cloning, purification, and characterization of beta-cystathionase from Escherichia coli

1982

Dwivedi, C.M.; Ragin, R.C.; Uren, J.R.

Biochemistry

21

3064-3069

34691

14692

Sulphur metabolism in Paracoccus denitrificans. Purification, properties and regulation of serine transacetylase, O-acetylserine sulphydrylase and beta-cystathionase

1977

Burnell, J.N.; Whatley, F.R.

Biochim. Biophys. Acta

481

246-265

34698

-

Enzyme catalysed alpha,beta-elimination of selenocystathionine and selenocystine and their sulphur isologues by plant extracts

1986

McCluskey, T.J.; Scarf, A.R.; Anderson, J.W.

Phytochemistry

25

2063-2068

34708

-

Occurrence of two types of cystathionine beta-cleavage enzyme in Bacillus subtilis

1972

Sakata, T.; Hiroishi, S.; Kadota, H.

Agric. Biol. Chem.

36

333-335

34712

8463265

Toxicity of Bordetella avium beta-cystathionase toward MC3T3-E1 osteogenic cells

1993

Gentry-Weeks, C.R.; Keith, J.M.; Thompson, J.

J. Biol. Chem.

268

7298-7314

34713

7706318

beta-Cystathionase from Bordetella avium. Role(s) of lysine 214 and cysteine residues in activity and cytotoxicity

1995

Gentry-Weeks, C.R.; Spokes, J.; Thompson, J.

J. Biol. Chem.

270

7695-7702

34715

1898098

The C-S lyases of higher plants: homogeneous beta-cystathionase of spinach leaves

1991

Staton, A.L.; Mazelis, M.

Arch. Biochem. Biophys.

290

46-50

94688

20939

Rabbit muscle phosphorylase phosphatase. 1. Purification and chemical properties

1977

Gratecos, D.; Detwiler, T.C.; Hurd, S.; Fischer, E.H.

Biochemistry

16

4812-4817

134132

9722024

Characterization of fetal serum 5'-nucleotide phosphodiesterase: A novel function as a platelet aggregation inhibitor in fetal circulation

1998

Sakura, H.; Nagashima, S.; Nakashima, A.; Maeda, M.

Thromb. Res.

91

83-89

209746

10591020

Characterization of an inducible nitrilase from a thermophilic bacillus

1999

Almatawah, Q.A.; Cramp, R.; Cowan, D.A.

Extremophiles

3

283-291

285441

6965849

Activation and Inhibition of the adrenal steroid 21-hydroxylation system by cytosolic constituents: influence of glutathione, glutathione reductase, and ascorbate

1980

Greenfield, N.; Ponticorvo, L.; Chasalow, F.; Lieberman, S.

Arch. Biochem. Biophys.

200

232-244

391773

3188059

Purification and characterization of L-amino acid oxidase from the venom of Trimeresurus mucrosquamatus (Taiwan habu snake)

1988

Ueda, M.; Chang, C.C.; Ohno, M.

Toxicon

26

695-706

391775

-

Oxidative deamination of sulfur amino acids by bacterial and snake venom L-amino acid oxidase

1971

Chen, S.S.; Walgate, J.H.; Duerre, J.A.

Arch. Biochem. Biophys.

146

51-63

395014

5646485

A thiol-disulfide transhydrogenase from yeast

1968

Nagai, S.; Black, S.

J. Biol. Chem.

243

1942-1947

395015

-

Thiol-disulfide transhydrogenase (yeast)

1971

Nagai, S.

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