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Ligand S-(2-aminoethyl)-L-cysteine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (19 results)

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Show Substrate (19 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.2

(S)-aminoethylcysteine + O2 = ?

440274

-

1.13.12.2

L-thialysine + O2 = ?

440276

-

1.13.12.2

2 entries

1.14.13.59

(S)-2-Aminoethyl-L-Cys + NADPH + O2 = ?

207907, 207904

-

1.4.1.15

S-(2-aminoethyl)-L-cysteine + NADP+ + H2O = S-(2-oxoethyl)-L-cysteine + NADPH + NH3

391500

-

1.4.1.18

S-(beta-aminoethyl)-L-cysteine + NAD+ = ?

391527, 391532, 391533, 654286

-

1.5.1.24

S-(2-aminoethyl)-L- cysteine + pyruvate + NADPH + H+ = ? + NADP+ + H2O

712294

-

1.5.1.8

S-2-aminoethyl-L-cysteine + 2-oxoglutarate + NADPH = ?

392361, 392367

-

2.6.1.36

L-thialysine + 2-oxoglutarate = ? + L-glutamate

637023

-

2.6.1.36

S-(2-aminoethyl)-L-cysteine + 2-oxoglutarate = ? + L-glutamate

637018, 637023

-

2.6.1.36

2 entries

2.6.1.62

S-2-aminoethyl-L-cysteine + 8-amino-7-oxononanoate = ? + (7S,8R)-diaminononanoate

661370

-

2.6.1.64

S-aminoethyl-L-cysteine + phenylpyruvate = 2H-1,4-thiazine-5,6-dihydro-3-carboxylic acid + L-phenylalanine

640176

-

2.6.1.64

S-aminoethyl-L-cysteine + phenylpyruvate = S-aminoethyl-(3-mercapto-2-oxopropanoate) + L-phenylalanine

640176

-

2.6.1.64

2 entries

4.1.1.18

S-Aminoethyl-L-Cys = 1-Amino-2-(S-aminoethyl)mercaptoethane + CO2

37294, 37295, 37300, 37289, 37293

-

4.3.1.28

L-4-thialysine = ?

719006

-

4.4.1.1

S-(2-aminoethyl)-L-cysteine + H2O = NH3 + pyruvate + cysteamine

653162

-

4.4.1.1

S-aminoethyl-L-Cys = ?

34507

-

4.4.1.1

2 entries

4.4.1.13

S-(2-aminoethyl)-L-Cys + H2O = ?

34712

-

4.4.1.28

S-aminoethyl-L-cysteine + H2O = NH3 + pyruvate + cysteamine

34507, 748127

-

5.4.3.3

4-thia-(R)-lysine = ?

714347

-

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.22

L-serine + cysteamine = L-thialysine

-

-

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.4.1.15

5 mM, 2.32fold activation

391499

-

Inhibitor in Enzyme-catalyzed Reactions (24 results)

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Show Inhibitors (24 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.31

92% inhibition at 1 mM

288199

-

1.2.1.31

competitive with respect to alpha-aminoadipate, non-competitive with respect to both ATP and NADPH

288185

-

1.5.1.8

-

392360

-

1.5.1.8

inhibits when present in assay with L-lysine, possibly competitive with L-lysine

392367

-

2.3.3.14

-

737195

-

2.3.3.14

-

737195

-

2.3.3.14

1.1 mM required for half-maximal inhibition of enzyme from wild-type strain, enzyme from S-(beta-aminoethyl)-L-cysteine resistant mutant strain is not inhibited

488140

-

2.3.3.14

5 mM, complete inhibition

488138

-

2.3.3.14

competitive with acetyl-CoA

488141

-

2.3.3.14

L-thialysine

288192

-

1.2.1.31

2 entries

1.5.1.8

2 entries

2.3.3.14

6 entries

2.7.1.81

-

642034

-

2.7.2.4

L-threonine-analog; works as L-lysine analog

677773

-

2.7.2.4

less effective on the first isoenzyme than L-lysine alone

677561

-

2.7.2.4

2 entries

3.4.24.20

-

31045

-

3.7.1.3

0.001 mM in 0.06 mM Tris-HCl buffer

289267

-

4.1.1.20

-

4111

-

4.3.3.7

-

33902, 33903, 33911

-

4.3.3.7

4.6 mM, 50% inhibition

33912

-

4.3.3.7

I0.5: 0.4 mM

33903

-

4.3.3.7

3 entries

5.4.3.2

-

3375, 3377

-

5.4.3.3

-

3401

-

6.1.1.6

-

661087

-

6.1.1.6

competitive inhibitor

672141

-

6.1.1.6

2 entries

6.3.4.19

-

704642

-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

3.4.19.12

6isu, 3D-view

4.1.3.3

4aho, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.4.1.28

17.8

-

pH 8.3, 30°C

748127

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.5.1.8

17

-

-

392367

2.6.1.36

2

-

pH 8.0, 37°C

637018

4.1.1.18

3.4

-

-

37289

4.1.1.18

4.5

-

-

37294, 37295

4.1.1.18

2 entries

4.4.1.1

2.75

-

pH 8.0, 37°C

653162

4.4.1.13

0.47

-

-

34712

4.4.1.28

0.27

-

pH 8.3, 30°C

748127

K_i Value (25 results)

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Show KI Value (25 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.2.1.31

0.007

-

-

288185

2.3.3.14

0.94

-

competitive against acetyl-CoA

488141

2.3.3.14

15

-

-

288192

2.3.3.14

2 entries

4.3.3.7

4.6

-

-

33912

6.1.1.6

0.0015

-

pH 7.2, 37°C, mutant enzyme E428Q

661087

6.1.1.6

0.0031

-

pH 7.2, 37°C, mutant enzyme E240D

661087

6.1.1.6

0.0039

-

pH 7.2, 37°C, wild-type enzyme

661087

6.1.1.6

0.004

-

pH 7.2, 37°C, mutant enzyme N424D

661087

6.1.1.6

0.005

-

pH 7.2, 37°C, mutant enzyme E278Q

661087

6.1.1.6

0.0054

-

pH 7.2, 37°C, mutant enzyme E240Q

661087

6.1.1.6

0.025

-

pH 7.2, 37°C, mutant enzyme F426W

661087

6.1.1.6

0.034

-

pH 7.2, 37°C, mutant enzyme E428D

661087

6.1.1.6

0.072

-

pH 7.2, 37°C, mutant enzyme Y280F

661087

6.1.1.6

0.076

-

pH 7.2, 37°C, mutant enzyme N424Q

661087

6.1.1.6

0.34

-

pH 7.2, 37°C, mutant enzyme Y280S

661087

6.1.1.6

1.24

-

pH 7.2, 37°C, mutant enzyme G216A

661087

6.1.1.6

1.29

-

pH 7.2, 37°C, mutant enzyme E278D

661087

6.1.1.6

1.31

-

pH 7.2, 37°C, mutant enzyme F426H

661087

6.1.1.6

2.9

-

mutant enzyme H242L

672141

6.1.1.6

3.6

-

wild type enzyme

672141

6.1.1.6

8.5

-

mutant enzyme H242A

672141

6.1.1.6

11

-

mutant enzyme W220L

672141

6.1.1.6

11.8

-

mutant enzyme G29A

672141

6.1.1.6

17

-

mutant enzyme W220Y

672141

6.1.1.6

19

-

mutant enzyme W220A

672141

6.1.1.6

21 entries

IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.3.3.14

1.8

-

isoform Lys22p, at pH 7.5 and 22°C

737195

2.3.3.14

16.5

-

isoform Lys21p, at pH 7.5 and 22°C

737195

2.3.3.14

2 entries

6.3.4.19

0.000045

-

pH 8.5, 21°C

704642

References & Links

Literature References (52)

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Show Reference (52 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

3375

5438361

Lysine 2,3-aminomutase. Purification and properties of a pyridoxal phosphate and S-adenosylmethionine-activated enzyme

1970

Chirpich, T.P.; Zappia, V.; Costilow, R.N.; Barker, H.A.

J. Biol. Chem.

245

1778-1789

3377

-

Lysine-2,3-aminomutase (Clostridium)

1971

Chirpich, T.P.; Barker, H.A.

Methods Enzymol.

17B

215-222

3401

5480154

Studies on the fermentation of D-alpha-lysine. Purification and properties of an adenosine triphosphate regulated B12-coenzyme-dependent D-alpha-lysine mutase complex from Clostridium sticklandii

1970

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

Biochemistry

9

4890-4900

4111

234936

Control of lysine biosynthesis in Bacillis subtilis: inhibition of diaminopimelate decarboxylase by lysine

1975

Rosner, A.

J. Bacteriol.

121

20-28

31045

23849

Specificity and inhibition studies of Armillaria mellea protease

1978

Lewis, W.G.; Basford, J.M.; Wlatoon, P.L.

Biochim. Biophys. Acta

522

551-560

33902

16665646

Purification and characterization of dihydrodipicolinate synthase from wheat suspension cultures

1987

Kumpaisal, R.; Hashimoto, T.; Yamada, Y.

Plant Physiol.

85

145-151

33903

-

Spinach leaf dihydrodipicolinate synthase: partial purification and characterization

1981

Wallsgrove, R.M.; Mazelis, M.

Phytochemistry

20

2651-2655

33911

16668206

Isolation and characterization of dihydrodipicolinate synthase from maize

1991

Frisch, D.A.; Gengenbach, B.G.; Tommy, A.M.; Sellner, J.M.; Somers, D.A.; Myers, D.E.

Plant Physiol.

96

444-452

33912

-

Escherichia coli dihydrodipicolinate synthase. Identification of the active site and crystallization

1992

Laber, B.; Gomis-Rueth, F.X.; Romao, M.J.; Huber, R.

Biochem. J.

268

691-695

34507

10194060

Cystalysin, a 46-kDa L-cysteine desulfhydrase from Treponema denticola: biochemical and biophysical characterization

1999

Chu, L.; Ebersole, J.L.; Kurzban, G.P.; Holt, S.C.

Clin. Infect. Dis.

28

442-450

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

37289

6353151

Lysine decarboxylase (Escherichia coli B)

1983

Boeker, E.A.; Fischer, E.H.

Methods Enzymol.

94

180-184

37293

4590109

Purification and physical properties of inducible Escherichia coli lysine decarboxylase

1974

Sabo, D.L.; Boeker, E.A.; Byers, B.; Waron, H.; Fischer, E.H.

Biochemistry

13

662-670

37294

-

L-Lysine decarboxylase (Bacterium cadaveris)

1971

Soda, K.; Moriguchi, M.

Methods Enzymol.

17B

677-681

37295

5762458

Crystalline lysine decarboxylase

1969

Soda, K.; Moriguchi, M.

Biochem. Biophys. Res. Commun.

34

34-39

37300

1799949

Purification and some properties of inducible lysine decarboxylase from Vibrio parahaemolyticus

1991

Yamamoto, S.; Imamura, T.; Kusaba, K.; Shinoda, S.

Chem. Pharm. Bull.

39

3067-3070

207904

2518519

Isolation and some properties of lysine N6-hydroxylase from Escherichia coli strain EN222

1989

Plattner, H.J.; Pfefferle, P.; Romaguera, A.; Waschutza, S.; Dieckman, H.

Biol. Met.

2

1-5

207907

8218389

Physico-chemical characterization of a recombinant cytoplasmic form of lysine:N6-hydroxylase

1993

Thariath, A.M.; Fatum, K.L.; Valvano, M.A.; Viswanatha, T.

Biochim. Biophys. Acta

1203

27-35

288185

1975789

Inhibition of alpha-aminoadipate-semialdehyde dehydrogenase from Trichosporon adeninovorans by lysine and lysine analogues

1990

Schmidt, H.; Bode, R.; Birnbaum D.

FEMS Microbiol. Lett.

70

41-44

288192

-

Lysine biosynthesis in the yeast Candida maltosa: properties of some enzymes and regulation of the biosynthetic pathway

1985

Schmidt, H.; Bode, R.; Lindner, M.; Birnbaum, D.

J. Basic Microbiol.

25

675-681

288199

9560434

Molecular analysis of the LYS2 gene of Candida albicans: homology to peptide antibiotic synthetases and the regulation of the.alpha-aminoadipate reductase

1998

Suvarna, K.; Seah, L.; Bhattacherjee, V.; Bhattacharjee, J.K.

Curr. Genet.

33

268-275

289267

158014

Inducible and constitutive kynureninases. Control of the inducible enzyme activity by transamination and inhibition of the constitutive enzyme by 3-hydroxyanthranilate

1979

Tanizawa, K.; Soda, K.

J. Biochem.

86

499-508

391499

-

NAD+-dependent lysine dehydrogenase from a plant-pathogenic bacterium, Agrobacterium tumefaciens

1991

Misono, H.

Vitamins (Kyoto)

65

1-12

391500

1509828

Enzymic production of alpha-aminoadipate-delta-semialdehyde and related compounds by lysine epsilon-dehydrogenase from Candida albicans

1992

Hammer, T.; Bode, R.

Zentralbl. Mikrobiol.

147

65-70

391527

2777754

Purification and properties of L-lysine epsilon-deydrogenase from Agrobacterium tumefaciens

1985

Misono, H.; Uehigashi, H.; Morimoto, E.; Nagasaki, S.

Agric. Biol. Chem.

49

2253-2255

391532

2768207

Properties of L-lysine epsilon-dehydrogenase from Agrobacterium tumefaciens

1989

Misono, H.; Hashimoto, H.; Uehigashi, H.; Nagata, S.; Nagasaki, S.

J. Biochem.

105

1002-1008

391533

2777754

Activation of L-lysine epsilon-dehydrogenase from Agrobacterium tumefaciens by several amino acids and monocarboxylates

1989

Hashimoto, H.; Misono, H.; Nagata, S.; Nagasaki, S.

J. Biochem.

106

76-80

392360

1169916

Purification and properties of L-lysine-alpha-ketoglutarate reductase from human placenta

1975

Fjellstedt, T.A.; Robinson, J.C.

Arch. Biochem. Biophys.

168

536-548

392361

235294

Lysine-ketoglutarate reductase in human tissues

1975

Hutzler, J.; Dancis, J.

Biochim. Biophys. Acta

377

42-51

392367

-

Degradation of lysine in rice seeds: Effect of calcium, ionic strength, S-adenosylmethionine and S-2-aminoethyl-L-cysteine on the lysine 2-oxoglutarate reductase-saccharopine dehydrogenase bifunctional enzyme

2000

Gaziola, S.A.; Sodek, L.; Arruda, P.; Lea, P.J.; Azevedo, R.A.

Physiol. Plant.

110

164-171

440274

4624115

Studies on monooxygenases. V. Manifestation of amino acid oxidase activity by L-lysine monooxygenase

1972

Nakazawa, T.; Hori, K.; Hayaishi, O.

J. Biol. Chem.

247

3439-3444

440276

-

Lysine oxygenase (Pseudomonas)

1971

Nakazawa, T.

Methods Enzymol.

17B

154-157

488138

792390

Biosynthesis of lysine in Saccharomyces cerevisiae: Regulation of homocitrate synthase in analogue-resistant mutants

1976

Gray, G.S.; Bhattacharjee, J.K.

J. Gen. Microbiol.

97

117-120

488140

-

Homocitrate synthase of S-(beta-aminoethyl)-L-cysteine resistant mutant of Candida pelliculosa

1981

Takenouchi, E.; Tanaka, H.; Soda, K.

J. Ferment. Technol.

59

429-433

488141

-

Effects of a selenium analogue of L-lysine on growth of Candida pelliculosa

1984

Shimizu, E.; Yamana, R.; Tanaka, H.; Soda, K.

Agric. Biol. Chem.

48

2871-2872

637018

-

L-Lysine-ketoglutarate aminotransferase (Acetobacter liquidum)

1971

Soda, K.; Misono, H.

Methods Enzymol.

17B

222-228

637023

1527704

Purification and characterization of an inducible L-lysine: 2-oxoglutarate 6-aminotransferase from Candida utilis

1992

Hammer, T.; Bode, R.

J. Basic Microbiol.

32

21-27

640176

3709533

The transamination of L-cystathionine, L-cystine and related compounds by a bovine kidney transaminase

1986

Ricci, G.; Nardini, M.; Federici, G.; Cavallini, D.

Eur. J. Biochem.

157

57-63

642034

4621658

The partial purification and properties of hydroxylysine kinase from rat liver

1972

Hiles, R.A.; Henderson, LaVell M.

J. Biol. Chem.

247

646-651

653162

12480900

lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine

2002

Yoshida, Y.; Nakano, Y.; Amano, A.; Yoshimura, M.; Fukamachi, H.; Oho, T.; Koga, T.

Microbiology

148

3961-3970

654286

14766574

Highly stable L-lysine 6-dehydrogenase from the thermophile Geobacillus stearothermophilus isolated from a Japanese hot spring: characterization, gene cloning and sequencing, and expression

2004

Heydari, M.; Ohshima, T.; Nunoura-Kominato, N.; Sakuraba, H.

Appl. Environ. Microbiol.

70

937-942

661087

15362869

Discrimination of cognate and noncognate substrates at the active site of class II lysyl-tRNA synthetase

2004

Ataide, S.F.; Ibba, M.

Biochemistry

43

11836-11841

661370

15880481

Removing a bottleneck in the Bacillus subtilis biotin pathway: bioA utilizes lysine rather than S-adenosylmethionine as the amino donor in the KAPA-to-DAPA reaction

2005

Van Arsdell, S.W.; Perkins, J.B.; Yocum, R.R.; Luan, L.; Howitt, C.L.; Chatterjee, N.P.; Pero, J.G.

Biotechnol. Bioeng.

91

75-83

672141

16533047

Discrimination of cognate and noncognate substrates at the active site of class I lysyl-tRNA synthetase

2006

Wang, S.; Praetorius-Ibba, M.; Ataide, S.F.; Roy, H.; Ibba, M.

Biochemistry

45

3646-3652

677561

100109407

Lysine and threonine biosynthesis in sorghum seeds: characterisation of aspartate kinase and homoserine dehydrogenase isoenzymes

2006

Ferreira, R.R.; Meinhardt, L.W.; Azevedo, R.A.

Ann. Appl. Biol.

149

77-86

677773

17611754

varepsilon-Poly-L-lysine producer, Streptomyces albulus, has feedback-inhibition resistant aspartokinase

2007

Hamano, Y.; Nicchu, I.; Shimizu, T.; Onji, Y.; Hiraki, J.; Takagi, H.

Appl. Microbiol. Biotechnol.

76

873-882

704642

19233850

The catalytic flexibility of tRNAIle-lysidine synthetase can generate alternative tRNA substrates for isoleucyl-tRNA synthetase

2009

Salowe, S.P.; Wiltsie, J.; Hawkins, J.C.; Sonatore, L.M.

J. Biol. Chem.

284

9656-9662

712294

19933367

The gene CBO0515 from Clostridium botulinum strain Hall A encodes the rare enzyme N5-(carboxyethyl) ornithine synthase, EC 1.5.1.24

2010

Thompson, J.; Hill, K.K.; Smith, T.J.; Pikis, A.

J. Bacteriol.

192

1151-1155

714347

21435400

Pyridoxal-5'-phosphate as the catalyst for radical isomerization in reactions of PLP-dependent aminomutases

2011

Frey, P.A.; Reed, G.H.

Biochim. Biophys. Acta

1814

1548-1557

719006

17291665

Biochemical characterisation of recombinant Streptomyces pristinaespiralis L-lysine cyclodeaminase

2007

Tsotsou, G.E.; Barbirato, F.

Biochimie

89

591-604

737195

26363118

Characterization of recombinant homocitrate synthase from Candida albicans

2016

Gabriel, I.; Milewski, S.

Protein Expr. Purif.

125

7-18

748127

28003427

Characterization of C-S lyase from Lactobacillus delbrueckii subsp. bulgaricus ATCC BAA-365 and its potential role in food flavour applications

2017

Allegrini, A.; Astegno, A.; La Verde, V.; Dominici, P.

J. Biochem.

161

349-360

Links to other databases for S-(2-aminoethyl)-L-cysteine

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Show Links (1 entry)

ChEBI

PubChem

-