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Ligand beta-chloro-L-alanine

Basic Ligand Information

Molecular Structure

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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

4.4.1.9

chloroalanine + sulfide = L-cysteine + Cl-

652652

-

Substrate in Enzyme-catalyzed Reactions (45 results)

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Show Substrate (45 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.47

3-chloro-L-alanine + NaHS = L-cysteine + ?

637349

-

2.5.1.47

beta-chloro-L-alanine + 2-nitro-5-thiobenzoate = ?

661281

-

2.5.1.47

chloroalanine + sulfide = cysteine + chloride

637383, 637378

-

2.5.1.65

3-chloro-L-alanine + hydrogen sulfide = ?

655576

-

2.5.1.65

3-chloro-L-alanine + sulfide = ?

655576

-

2.5.1.47

3 entries

2.5.1.65

2 entries

2.6.1.42

beta-chloro-L-alanine + ? = 3-chloropyruvate + ?

640043

-

2.6.1.9

beta-chloro-L-alanine = pyruvate + NH3 + Cl-

637144

-

3.7.1.3

beta-chloro-L-alanine + H2O = ?

289274

-

4.1.1.12

beta-chloro-L-Ala + H2O = pyruvate + Cl- + NH4+

3955

-

4.1.99.1

beta-chloro-L-Ala + H2O = ?

713955

-

4.1.99.1

beta-chloroalanine + H2O = ?

37335, 37341

-

4.1.99.1

beta-chloroalanine + H2O = pyruvate + NH4+ + Cl-

664234

-

4.1.99.2

3-chloro-L-Ala + H2O = ?

33472, 33471, 678401, 33465

-

4.1.99.2

beta-chloro-L-alanine + H2O = ?

650404, 651817

-

4.1.99.2

beta-chloro-L-alanine + H2O = Cl- + pyruvate + NH3

746892

-

4.1.99.2

beta-chloro-L-alanine = ?

653702, 649731

-

4.2.1.20

beta-chloro-L-alanine + indole = L-tryptophan + HCl

649903

-

4.2.1.20

beta-chloro-L-alanine = pyruvate + NH3 + HCl

649903

-

4.1.99.1

3 entries

4.1.99.2

4 entries

4.2.1.20

2 entries

4.3.1.10

beta-chloroalanine = ?

6034, 6039

-

4.3.1.17

beta-chloro-L-alanine = 3-chloropropenoic acid + NH3

661171

-

4.3.1.19

beta-chloro-L-Ala = ?

210824, 210830

-

4.3.1.19

beta-chloro-L-alanine = 3-chloro-2-oxopropionate + NH3

747154

-

4.4.1.1

beta-chloro-L-Ala = ?

586904

-

4.4.1.1

beta-chloro-L-alanine + H2O = pyruvate + NH3 + HCl

664075, 665558

-

4.3.1.19

2 entries

4.4.1.1

2 entries

4.4.1.11

beta-chloro-L-alanine + H2O = ?

691377

-

4.4.1.13

beta-chloro-L-alanine = ?

640043

-

4.4.1.13

beta-chloroalanine = ?

34542

-

4.4.1.13

2 entries

4.4.1.16

beta-chloro-L-alanine = NH3 + pyruvate + chloride

648741, 648743

-

4.4.1.28

beta-chloro-L-alanine + H2O = sulfide + ?

730534

-

4.4.1.4

beta-chloro-L-Ala = ?

34609

-

4.4.1.9

3-chloro-L-alanine + HCN = ?

34716

-

4.4.1.9

chloroalanine + sulfide = L-cysteine + Cl-

637378, 652652

-

4.5.1.5

3-chloro-L-alanine + 1-thioglycerol = S-2,3-dihydroxypropyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + 2-mercaptoethanol = S-2-hydroxyethyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + benzylmercaptan = S-benzyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + ethylmercaptan = S-ethyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + methylmercaptan = S-methyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + n-propylmercaptan = S-propyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + phenylmercaptan = S-phenyl-L-cysteine + Cl-

648766

-

4.5.1.5

3-chloro-L-alanine + thioglycolate = S-carboxymethyl-L-cysteine + Cl-

648766

-

4.4.1.9

2 entries

4.5.1.5

8 entries

5.1.1.18

beta-chloro-L-alanine = pyruvate + NH3 + ?

714348

-

6.3.2.13

ATP + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamate + beta-chloro-L-alanine = ADP + phosphate + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-beta-chloro-L-alanine

744440

-

6.3.2.2

ATP + L-Glu + beta-chloro-L-Ala = ADP + phosphate + gamma-L-Glu-L-beta-chloro-L-Ala

1118, 1122, 1131

-

6.3.2.2

ATP + L-Glu + beta-chloro-L-alanine = ADP + phosphate + gamma-L-Glu-beta-chloro-L-alanine

652341, 649263

-

6.3.2.2

2 entries

6.3.2.8

ATP + UDP-N-acetylmuramate + beta-chloro-L-Ala = ADP + phosphate + UDP-N-acetylmuramoyl-beta-chloro-L-Ala

1289, 1290

-

Inhibitor in Enzyme-catalyzed Reactions (41 results)

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Show Inhibitors (41 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.1.2.1

suicide substrate

441411

-

2.3.1.50

-

487159, 487166, 487174

-

2.3.1.50

cytotoxic, irreversible

487170

-

2.3.1.50

in vivo, time dependent

487165

-

2.3.1.50

irreversible

658020

-

2.3.1.50

mechanism-based inhibition

487168

-

2.3.1.50

rapid, irreversible and time dependent inhibition at the active site; stereospecific, no inhibition by beta-chloro-D-alanine; suicide substrate

487165

-

2.3.1.50

6 entries

2.3.2.2

-

487946

-

2.5.1.47

substrate inhibition

637378

-

2.6.1.2

0.1 mM, 78% inhibition

636731

-

2.6.1.2

-

737484

-

2.6.1.2

2 entries

2.6.1.4

-

636731

-

2.6.1.42

rapidly inactivated by the beta-lyase substrate

640043

-

2.6.1.42

the compound is able to fit into the active site of BCATm, leading to inhibition of BCATm

758657

-

2.6.1.42

2 entries

2.6.1.43

-

640059

-

2.6.1.45

-

636693

-

2.6.1.45

reacts with the carbonyl group of pyridoxal phosphate. 53.9% inhibition at 1 mM

684122

-

2.6.1.45

competitive vs. L-alanine, uncompetitive vs. 2-oxomalonate

636701

-

2.6.1.45

3 entries

2.6.1.66

-

737484

-

3.5.99.7

-

648246, 648251

-

3.5.99.7

mechanism-based inhibition

648247

-

3.5.99.7

2 entries

3.7.1.3

irreversible inhibition

658274

-

4.1.1.12

reacts with a specific glutamic acid residue at the active center of the enzyme

3956

-

4.2.1.22

-

5603

-

4.3.1.13

irreversible

6042

-

4.4.1.16

-

648743

-

4.4.1.16

irreversible

648741

-

4.4.1.9

substrate inhibition

637378

-

4.4.1.9

uncompetitive vs. L-cysteine

652652

-

4.4.1.16

2 entries

4.4.1.9

2 entries

4.5.1.2

competitive

34749

-

5.1.1.1

-

748310

-

5.1.1.1

effective in the inhibition of bacterial growth like that of the D-isomer. But the L-isomer has less specificity towards the concerned Alr enzymes due to its inhibitory activity towards decarboxylase and transaminases. This results in the blockage of the production of essential L-amino acids with a loss of viability of bacterial and mammalial cells

748310

-

5.1.1.1

-

716705

-

5.1.1.1

enantiomers of beta-chloroalanine as Alr inhibitors

748310

-

5.1.1.1

-

2015

-

5.1.1.1

-

2015

-

5.1.1.1

Ki: 1.71 mM, noncompetitive

2011

-

5.1.1.1

7 entries

5.1.1.10

inactivator binds to the same Lys residue which binds pyridoxyl 5'-phosphate

2043

-

5.1.1.18

2 mM, 68% residual activity

661410

-

5.1.1.3

BCLA, modifies BsMurI predominantly at C74, the cysteine residue responsible for deprotonation of an incoming D-Glu substrate

746766

-

6.3.2.8

-

1277, 1286, 1287, 1288, 1289

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (18 results)

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Show Turnover Number (18 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.5.1.47

154

-

pH 7.0, 50°C

661281

4.1.99.1

0.0932

-

pH 7.8, 37°C, mutant enzyme Y72F

664234

4.1.99.1

3

-

pH 8.0, 25°C

713955

4.1.99.1

12.4

-

pH 8.0, 25°C

713955

4.1.99.2

0.0065

-

mutant enzyme D214N, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

0.02

-

mutant enzyme D214A, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

0.053

-

mutant enzyme Y71F

33471

4.1.99.2

0.15

-

recombinant mutant S51A, pH 8.0, 30°C

746892

4.1.99.2

0.7

-

wild type enzyme, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

0.7

-

wild-type enzyme

33471

4.1.99.2

1.13

-

mutant enzyme R100T/V283R

33472

4.1.99.2

3

-

wild-type enzyme

33472, 33470

4.1.99.2

6

-

recombinant wild-type enzyme, pH 8.0, 30°C

746892

4.1.99.1

3 entries

4.1.99.2

9 entries

4.3.1.17

2.6

-

pH 8.0, 37°C, presence of 1 mM ATP, elimination reaction

661171

4.3.1.19

27.15

-

pH 8.0, 30°C

747154

4.4.1.28

14.5

-

pH and temperature not specified in the publication, addition of Brij 35 to the assay buffer

730534

6.3.2.8

11.1

-

-

1289

6.3.2.8

20

-

-

1290

6.3.2.8

2 entries

K_M Value (32 results)

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Show KM Value (32 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.5.1.47

0.785

-

pH 8.0, 26°C, cysteine synthase B

637378

2.5.1.47

1.053

-

pH 8.0, 26°C, cysteine synthase A

637378

2.5.1.47

2 entries

2.6.1.42

0.6

-

pH 7.4, 23°C, recombinant BCATm

640043

4.1.1.12

0.063

-

-

3955

4.1.99.1

1.2

-

-

37335

4.1.99.1

1.2

-

strain B/1t7-A

37341

4.1.99.1

6.15

-

pH 7.8, 37°C, mutant enzyme Y72F

664234

4.1.99.2

0.8

-

recombinant mutant S51A, pH 8.0, 30°C

746892

4.1.99.2

1.7

-

wild-type enzyme

33472

4.1.99.2

2

-

mutant enzyme Y71F

33471

4.1.99.2

2

-

wild type enzyme, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

2.12

-

recombinant wild-type enzyme, pH 8.0, 30°C

746892

4.1.99.2

3.2

-

mutant enzyme Y71F

33471

4.1.99.2

10.2

-

-

33465

4.1.99.2

11.4

-

mutant enzyme D214N, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

12

-

pH 7.2, 60°C

651817

4.1.99.2

13.3

-

mutant enzyme D214A, in 50 mM potassium phosphate pH 8.0, at 25°C

678401

4.1.99.2

46

-

mutant enzyme R100T/V283R

33472

4.1.99.1

3 entries

4.1.99.2

11 entries

4.3.1.19

3.01

-

pH 8.0, 30°C

747154

4.4.1.1

0.1

-

Y123F/Y124F mutant, 20 mM potassium phosphate buffer, pH 7.4, 25°C

665558

4.4.1.1

0.17

-

Y123F mutant, 20 mM potassium phosphate buffer, pH 7.4, 25°C

665558

4.4.1.1

1.21

-

wild type, 20 mM potassium phosphate buffer, pH 7.4, 25°C

665558

4.4.1.1

2.39

-

-

586904

4.4.1.1

3.2

-

Y124F mutant, 20 mM potassium phosphate buffer, pH 7.4, 25°C

665558

4.4.1.13

0.6

-

-

640043

4.4.1.13

2.6

-

-

34542

4.4.1.1

5 entries

4.4.1.13

2 entries

4.4.1.16

3.1

-

pH 7.2

648741

4.4.1.28

0.36

-

pH and temperature not specified in the publication, addition of Brij 35 to the assay buffer

730534

4.4.1.9

0.54

-

-

652652

4.4.1.9

0.6

-

26°C, pH 9.8

637378

4.4.1.9

2 entries

4.5.1.5

40

-

pH 7.8, 37°C

648766

6.3.2.8

0.173

-

-

1289

K_i Value (9 results)

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Show KI Value (9 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.5.1.47

0.8

-

pH 9.8, 26 C, cysteine synthase B

637378

2.5.1.47

1.135

-

pH 9.8, 26 C, cysteine synthase A

637378

2.5.1.47

5.546

-

pH 8.0, 26 C, cysteine synthase B

637378

2.5.1.47

70.92

-

pH 8.0, 26 C, cysteine synthase A

637378

2.5.1.47

4 entries

2.6.1.45

0.0036

-

pH 8.0

636701

4.4.1.16

2.5

-

-

648743

4.4.1.16

2.5

-

pH 7.2

648741

4.4.1.9

2.27

-

vs. L-cysteine

652652

4.4.1.9

6.9

-

26°C, pH 9.8

637378

4.4.1.16

2 entries

4.4.1.9

2 entries

IC₅₀ Value (2 results)

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Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.6.1.2

0.15

-

pH 8.0, temperature not specified in the publication

737484

2.6.1.66

20

-

above 20 mM, pH 8.0, temperature not specified in the publication

737484

References & Links

Literature References (86)

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Show Reference (86 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1118

2895925

On the active site thiol of gamma-glutamylcysteine synthetase: relationship to catalysis, inhibition, and regulation

1988

Huang, C.S.; Moore, W.R.; Meister, A.

Proc. Natl. Acad. Sci. USA

85

2464-2468

1122

2868388

Glutathione biosynthesis: gamma-Glutamylcysteine synthetase from rat kidney

1985

Seelig, G.F.; Meister, A.

Methods Enzymol.

113

379-390

1131

25775

Bovine lenticular gamma-glutamylcysteine synthetase: reaction sequence

1978

Van Buskirk, G.E.; Gander, J.E.; Rathbun, W.B.

Eur. J. Biochem.

85

589-597

1277

6811120

Inhibition of uridine 5¦-diphosphate-N-acetylmuramyl-L-alanine synthetase by beta-chloro-L-alanine in Escherichia coli

1982

Ishiguro, E.E.

Can. J. Microbiol.

28

654-659

1286

1855644

Effect of various alanine analogues on the L-alanine-adding enzyme from Escherichia coli

1991

Liger, D.; Blanot, D.; van Heijenoort, J.

FEMS Microbiol. Lett.

80

111-116

1287

9158719

Study of the overproduced uridine-diphosphate-N-acetylmuramate:L-alanine ligase from Escherichia coli

1996

Liger, D.; Masson, A.; Blanot, D.; van Heijenoort, J.; Parquet, C.

Microb. Drug Resist.

2

25-27

1288

7601127

Over-production, purification and properties of the uridine-diphosphate-N-acetylmuramate:L-alanine ligase from Escherichia coli

1995

Liger, S.; Masson, A.; Blanot, D.; van Heijenoort, J.; Parquet, C.

Eur. J. Biochem.

230

80-87

1289

8550531

Overexpression, purification and characterization of UDP-N-acetylmuramyl:L-alanine ligase from Escherichia coli

1996

Gubler, M.; Appold, Y.; Keck, W.

J. Bacteriol.

178

906-910

1290

8976565

Kinetic and crystallographic studies of Escherichia coli UDP-N-acetylmuramate:L-alanine ligase

1996

Emanuele, J.J.; Jin, H.; Jacobson, B.L.; Chang, C.Y.; Einspahr, H.M.; Villafranca, J.J.

Protein Sci.

5

2566-2574

2011

816355

Inhibition studies of the enantiomers of beta-chloroalanine on purified alanine racemase from Bacillus subtilis

1976

Henderson, L.L.; Johnson, R.B.

Biochem. Biophys. Res. Commun.

68

793-798

2015

3524677

Biosynthetic alanine racemase of Salmonella typhimurium: purification and characterization of the enzyme encoded by the alr gene

1986

Esaki, N.; Walsh, C.T.

Biochemistry

25

3261-3267

2043

6439237

Inactivation of the Pseudomonas striata broad specificity amino acid racemase by D and L isomers of beta-substituted alanines: kinetics, stoichiometry, active site peptide, and mechanistic studies

1984

Roise, D.; Soda, K.; Yagi, T.; Walsh, C.T.

Biochemistry

23

5195-5201

3955

4950473

L-Aspartate-beta-decarboxylase. Structure, catalytic activities, and allosteric regulation

1971

Tate, S.S.; Meister, A.

Adv. Enzymol. Relat. Areas Mol. Biol.

35

503-543

3956

4817757

Affinity labeling of the active center of L-aspartate-beta-decarboxylase with beta-chloro-L-alanine

1974

Relyea, N.M.; Tate, S.S.; Meister, A.

J. Biol. Chem.

249

1519-1524

5603

8697099

A novel cystathionine beta-synthase from Panagrellus redivivus (Nematoda)

1996

Papadopoulos, A.I.; Walker, J.; Barrett, J.

Int. J. Biochem. Cell Biol.

28

543-549

6034

-

L-Serine O-sulphate-degrading system of rat liver

1971

Tudball, N.; Thomas, J.H.

Methods Enzymol.

17B

361-367

6039

5583990

Studies on the enzymic degradation of L-serine O-sulphate by a rat liver preparation

1967

Thomas, J.H.; Tudball, N.

Biochem. J.

105

467-472

6042

4761084

Enzymatic conversion of O-carbamyl-L-serine to pyruvate and ammonia

1973

Cooper, A.J.L.; Meister, A.

Biochem. Biophys. Res. Commun.

55

780-787

33465

-

Purification and properties of thermostable beta-tyrosinase from an obligate symbiotic thermophile, Symbiobacterium thermophilum

1992

Suzuki, S.; Hirahara, T.; Shim, J.K.; Horinouchi, S.; Beppu, T.

Biosci. Biotechnol. Biochem.

56

84-89

33470

9174368

The crystal structure of Citrobacter freundii tyrosine phenol-lyase complexed with 3-(4 -hydroxyphenyl)propionic acid, together with site-directed mutagenesis and kinetic analysis, demonstrates that arginine 381 is required for substrate specificity

1997

Sundaraju, B.; Antson, A.A.; Phillips, R.S.; Demidkina, T.V.; Barbolina, M.V.; Gollnick, P.; Dodson, G.G.; Wilson, K.S.

Biochemistry

36

6502-6510

33471

7547970

Site-directed mutagenesis of tyrosine-71 to phenylalanine in Citrobacter freundii tyrosine phenol-lyase: evidence for dual roles of tyrosine-71 as a general acid catalyst in the reaction mechanism and in cofactor binding

1995

Chen, H.Y.; Demidkina, T.V.; Phillips, R.S.

Biochemistry

34

12276-12283

33472

9880502

Conversion of tyrosine phenol-lyase to dicarboxylic amino acid beta-lyase, an enzyme not found in nature

1999

Mouratou, B.; Kasper, P.; Gehring, H.; Christen, P.

J. Biol. Chem.

274

1320-1325

34542

3003507

Cysteine conjugate beta-lyase

1985

Stevens, J.L.; Jacoby, W.B.

Methods Enzymol.

113

510-515

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

34716

-

Purification and properties of beta-cyano-L-alanine synthase from Vicia angustifolia

1989

Ikegami, F.; Takayama, K.; Kurihara, T.; Horiuchi, S.; Tajima, C.; Shirai, R.; Murakoshi, I.

Phytochemistry

28

2285-2291

34749

-

Synthesis of C-cysteine from a racemate of 3-chloroalanine by phenylhydrazine-treated cells of Pseudomonas putida CR 1-1

1983

Nagasawa, T.; Hosano, H.; Yamano, H.; Ohkishi, H.; Tani, Y.; Yamada, H.

Agric. Biol. Chem.

47

861-868

37335

3298983

Tryptophanase from Escherichia coli B/1t7-A

1987

Behbahani-Nejad, I.; Dye, J.L.; Suelter, C.H.

Methods Enzymol.

142

414-422

37341

236639

Tryptophanase: structure, catalytic activities, and mechanism of action

1975

Snell, E.E.

Adv. Enzymol. Relat. Areas Mol. Biol.

42

287-333

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Links to other databases for beta-chloro-L-alanine

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