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Ligand Acrylamide

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for Acrylamide

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.4

acrylamide + H2O = acrylic acid + NH3

209106

4izu, 3D-view

3.5.1.4

acrylamide + H2O = acrylic acid + NH3

209106

4izv, 3D-view

3.5.1.4

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.84

acrylonitrile + H2O = acrylamide

-

-

Substrate in Enzyme-catalyzed Reactions (16 results)

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Show Substrate (16 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.1

acrylamide + H2O = acrylic acid + NH3

755328

-

3.5.1.4

acrylamide + H2O = acrylate + NH3

655819, 209115, 712780, 753001, 209107, 209125, 209128, 733127, 718531, 719432, 718672, 711308, 684607, 712726

4izu, 3D-view

3.5.1.4

acrylamide + H2O = acrylate + NH3

655819, 209115, 712780, 753001, 209107, 209125, 209128, 733127, 718531, 719432, 718672, 711308, 684607, 712726

4izv, 3D-view

3.5.1.4

acrylamide + H2O = acrylic acid + NH3

209106, 667278, 724942, 671557, 699491

4izu, 3D-view

3.5.1.4

acrylamide + H2O = acrylic acid + NH3

209106, 667278, 724942, 671557, 699491

4izv, 3D-view

3.5.1.4

acrylamide + H2O = prop-2-enoic acid + NH3

209143, 666303

4izu, 3D-view

3.5.1.4

acrylamide + H2O = prop-2-enoic acid + NH3

209143, 666303

4izv, 3D-view

3.5.1.4

acrylamide + hydroxylamine = acrylhydroxamic acid + NH3

655819

4izu, 3D-view

3.5.1.4

acrylamide + hydroxylamine = acrylhydroxamic acid + NH3

655819

4izv, 3D-view

3.5.1.4

acrylamide + hydroxylamine = acryloylhydroxamic acid + NH3

684607

4izu, 3D-view

3.5.1.4

acrylamide + hydroxylamine = acryloylhydroxamic acid + NH3

684607

4izv, 3D-view

3.5.1.4

10 entries

3.5.1.49

acrylamide + H2O = acrylic acid + NH3

209145

-

3.5.1.84

prop-2-enamide + H2O = ?

718459

-

3.5.5.1

acrylamide + H2O = acrylic acid + NH3

757020

-

3.5.5.7

acrylamide + H2O = ?

655149

-

4.2.1.84

acrylamide + H2O = acrylonitrile

648454, 648456

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.66

acrylonitrile + H2O = acrylamide

-

-

4.2.1.84

acrylonitrile + H2O = 2-propenoic acid amide

, 648439, 648437, 648422, 648425, 648434, 648426, 648440, 648429, 648432

-

4.2.1.84

acrylonitrile + H2O = acrylamide

-

-

4.2.1.84

2 entries

Inhibitor in Enzyme-catalyzed Reactions (10 results)

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Show Inhibitors (10 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.7.3.2

CK-BB is kinetically reversibly inactivated by acrylamide accompanied by the disruption of the hydrophobic surface, complete inhibition at 800 mM

704051

-

2.7.3.2

significantly inactivate screatine kinase and glutathione S-transferase and deplete glutathione. When the dietary constituents, tea polyphenols, resveratrol, and diallyl trisulfide are cotreated with acrylamide, all of them can effectively recover the activities of creatine kinase

687261

-

3.5.1.4

substrate inhibition

684607

4izu, 3D-view

3.5.1.4

substrate inhibition

684607

4izv, 3D-view

4.2.1.84

-

673098

-

4.2.1.84

mutant enzyme S122C shows higher tolerance under increasing acrylamide levels than recombinant NHase with modified start codon only

675472

-

4.2.1.84

NHases exhibit low product acrylamide tolerance

730077

-

4.2.1.84

when the concentration of acrylamide is higher than 150 g/l, the activity of the immersed-NHase in free resting cells is significantly reduced, when the concentration is higher than 250 g/l, the deactivation is more serious and the half-life of the NHase is less than 120 min

703230

-

2.7.3.2

2 entries

3.5.1.4

2 entries

4.2.1.84

4 entries

5.6.1.4

kinesin inhibition is observed at acrylamide concentrations as low as 0.1 mM

698412

-

5.6.2.2

acrylamide is a catalytic inhibitor, no enzyme poison, it antagonizes the effect of etoposide, a topoisomerase II poison, and inhibits the enzyme in vivo in V-79 cells. Acrylamide reduces the level of catalytically active cellular topoisomerase II available for the action of etoposide. Assay in presence of DTT

706832

-

3D Structure of Enzyme-Ligand-Complex (PDB) (6 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (6 entries)

EC NUMBER

ENZYME 3D STRUCTURE

3.5.1.4

4izu, 3D-view

3.5.1.4

4izv, 3D-view

3.5.1.4

4izu, 3D-view

3.5.1.4

4izv, 3D-view

3.5.1.4

4izu, 3D-view

3.5.1.4

4izv, 3D-view

3.5.1.4

6 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (7 results)

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Show Turnover Number (7 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.5.1.4

0.0715

-

pH 8.0, 50°C

733127

3.5.1.4

0.58

-

-

699491

3.5.1.4

2.1

-

pH 5.9, 55°C, recombinant wild-type enzyme

711308

3.5.1.4

2.1

-

pH and temperature not specified in the publication

753001

3.5.1.4

8.3

-

pH 7.5, 70°C

719432

3.5.1.4

38.7

-

pH 7.2

684607

3.5.1.4

333.3

-

pH 7.6, 60°C

724942

3.5.1.4

7 entries

K_M Value (16 results)

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Show KM Value (16 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.4

1.2

-

-

209106

3.5.1.4

1.7

-

-

209115

3.5.1.4

2

-

mutant strain MM8

209107

3.5.1.4

2.39

-

pH 7.5, 30°C

718531

3.5.1.4

2.39

-

pH 8.0, 40°C

718531

3.5.1.4

2.8

-

pH 7.0, 35°C, recombinant enzyme

718672

3.5.1.4

3

-

acyl transfer reaction on hydroxylamine, pH = 7

655819

3.5.1.4

3

-

pH 7.5, 70°C

719432

3.5.1.4

4.79

-

-

699491

3.5.1.4

10.54

-

pH 8.0, 50°C

733127

3.5.1.4

10.86

-

pH 7.6, 60°C

724942

3.5.1.4

16

-

mutant strain 19

209125

3.5.1.4

24.1

-

pH 5.9, 55°C, recombinant wild-type enzyme

711308

3.5.1.4

24.1

-

pH and temperature not specified in the publication

753001

3.5.1.4

43.8

-

pH 7.2

684607

3.5.1.4

93

-

-

209128

3.5.1.4

16 entries

K_i Value (2 results)

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Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.4

2.3

-

at pH 7 and 50°C

684607

3.5.1.4

2.3

-

pH 7.2

684607

3.5.1.4

2 entries

References & Links

Literature References (45)

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Show Reference (45 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

209106

7944367

Purification and characterization of an amidase from an acrylamide-degrading Rhodococcus sp.

1994

Nawaz, S.M.; Khan, A.A.; Seng J.E.; Leakey, J.E.; Siitonen, P.H.; Cerniglia, C.E.

Appl. Environ. Microbiol.

60

3343-3348

209107

-

Directed evolution of amidase in Methylophilus methylotrophus; purification and properties of amidases from wild-type and mutants strains

1991

Silman, N.J.; Carver, A.M.; Jones, C.W.

J. Gen. Microbiol.

137

169-178

209115

8636044

Physical, biochemical, and immunological characterization of a thermostable amidase from Klebsiella pneumoniae NCTR 1

1996

Nawaz, M.S.; Khan, A.A.; Bhattacharayya, D.; Siitonen, P.H.; Cerniglia, C.E.

J. Bacteriol.

178

2397-2401

209125

-

Activity and regulation of an amidase, acylamide amidohydrolase EC 3.5.1.4, with a wide substrate spectrum from a Brevibacterium sp.

1984

Maestracci, M.; Thiery, A.; Bui, K.; Arnaud, A.; Galzy, P.

Arch. Microbiol.

138

315-320

209128

-

Acyltransferase activity of the wide spectrum amidase of Brevibacterium sp. R312

1986

Thiery, A.; Maestracci, M.; Arnaud, A.; Galzy, P.

J. Gen. Microbiol.

132

2205-2208

209143

9364923

Identification and characterization of an aliphatic amidase in Helicobacter pylori

1997

Skouloubris, S.; Labigne, A.; de Reuse H.

Mol. Microbiol.

25

989-998

209145

-

Purification, properties and heterologous expression of formamidase from Methylophilus methylotrophus

1994

Wyborn N.R.; Scherr, D.J.; Jones, C.W.

Microbiology

140

191-195

648422

-

Aliphatic nitrile hydratase from Arthrobacter sp. J-1. Purification and characterization

1982

Asano, Y.; Fujishiro, K.; Tani, Y.; Yamada, H.

Agric. Biol. Chem.

46

1165-1174

648425

-

Isolation and characterization of a nitrile hydratase from Rhodococcus sp.

1990

Hjort, C.M.; Godtfredsen, S.E.; Emborg, C.

J. Chem. Technol. Biotechnol.

48

217-226

648426

-

A nitrile hydratase with a wide substrate spectrum produces by a Brevibacterium sp.

1984

Bui, K.; Fradet, H.; Arnaud, A.; Galzy, P.

J. Gen. Microbiol.

130

89-93

648429

-

Formation and purification of nitrile hydratase from Corynebacterium pseudodiphteritium ZBB-41

1992

Li, W.Z.; Zhang, Y.Q.; Yang, H.F.

Appl. Biochem. Biotechnol.

36

171-181

648432

3768004

Nitrile hydratase of Brevibacterium R312 -Purification and characterization-

1986

Nagasawa, T.; Ryuno, K.; Yamada, H.

Biochem. Biophys. Res. Commun.

139

1305-1312

648434

-

Purification and properties of the nitrile hydratase of a new strain of Rhodococcus sp.

1991

Kaakeh, M.R.; Legras, J.L.; Duran, R.; Chion, Ch.K.N.C.K.; Arnaud, A.; Galzy, P.

Zentralbl. Mikrobiol.

146

89-98

648437

-

Characterization of nitrile hydratase and amidase, which are responsible for the conversion of dinitriles to mononitriles from Corynebacterium sp.

1989

Tani, Y.; Kurihara, M.; Nishise, H.

Agric. Biol. Chem.

53

3151-3158

648439

2013281

Characterization of a new cobalt-containing nitrile hydratase purified from urea-induced cells of Rhodococcus rhodochrous J1

1991

Nagasawa, T.; Takeuchi, K.; Yamada, H.

Eur. J. Biochem.

196

581-589

648440

3830164

Nitrile hydratase of Pseudomonas chlororaphis B23. Purification and characterization

1987

Nagasawa, T.; Nanba, H.; Ryuno, K.; Takeuchi, K.; Yamada, H.

Eur. J. Biochem.

162

691-698

648454

9702770

Metalloenzyme nitrile hydratase: structure, regulation, and application to biotechnology

1998

Kobayashi, M.; Shimizu, S.

Nat. Biotechnol.

16

733-736

648456

10742253

Nitrile hydratase and amidase from Rhodococcus rhodochrous hydrolyze acrylic fibers and granular polyacrylonitriles

2000

Tauber, M.M.; Cavaco-Paulo, A.; Robra, K.; Gubitz, G.M.

Appl. Environ. Microbiol.

66

1634-1638

655149

10913974

Enzymatic degradation of nitriles by a Candida guilliermondii UFMG-Y65

2000

Dias, J.C.T.; Rezende, R.P.; Rosa, C.A.; Lachance, M.A.; Linardi, V.R.

Can. J. Microbiol.

46

525-531

655819

11556902

Aliphatic and enantioselective amidases: from hydrolysis to acyl transfer activity

2001

Fournand, D.; Arnaud, A.

J. Appl. Microbiol.

91

381-393

666303

11434308

Substitutions of Thr-103-Ile and Trp-138-Gly in amidase from Pseudomonas aeruginosa are responsible for altered kinetic properties and enzyme instability

2001

Karmali, A.; Pacheco, R.; Tata, R.; Brown, P.

Mol. Biotechnol.

17

201-212

667278

15103424

Purification and properties of an enantioselective and thermoactive amidase from the thermophilic actinomycete Pseudonocardia thermophila

2004

Egorova, K.; Trauthwein, H.; Verseck, S.; Antranikian, G.

Appl. Microbiol. Biotechnol.

65

38-45

671557

17136368

Remaining acetamide in acetonitrile degradation using nitrile hydratase- and amidase-producing microorganisms

2007

Kohyama, E.; Dohi, M.; Yoshimura, A.; Yoshida, T.; Nagasawa, T.

Appl. Microbiol. Biotechnol.

74

829-835

673098

-

Inducing expression and reaction characteristic of nitrile hydratase from Rhodococcus sp. SHZ-1

2007

Wang, C.; Zhang, G.; Xu, X.; Li, C.

Chin. J. Chem. Engin.

15

573-578

675472

-

An over expression and high efficient mutation system of a cobalt-containing nitrile hydratase

2006

Yu, H.; Shi, Y.; Luo, H.; Tian, Z.; Zhu, Y.; Shen, Z.

J. Mol. Catal. B

43

80-85

684607

17347819

A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity

2007

Makhongela, H.S.; Glowacka, A.E.; Agarkar, V.B.; Sewell, B.T.; Weber, B.; Cameron, R.A.; Cowan, D.A.; Burton, S.G.

Appl. Microbiol. Biotechnol.

75

801-811

687261

18624451

Inhibition of acrylamide toxicity in mice by three dietary constituents

2008

Xie, Q.; Liu, Y.; Sun, H.; Liu, Y.; Ding, X.; Fu, D.; Liu, K.; Du, X.; Jia, G.

J. Agric. Food Chem.

56

6054-6060

698412

18624434

Inhibition of rat testicular nuclear kinesins (krp2; KIFC5A) by acrylamide as a basis for establishing a genotoxicity threshold

2008

Friedman, M.A.; Zeiger, E.; Marroni, D.E.; Sickles, D.W.

J. Agric. Food Chem.

56

6024-6030

699491

18388476

R-stereoselective amidase from Rhodococcus erythropolis No. 7 acting on 4-chloro-3-hydroxybutyramide

2008

Park, H.J.; Uhm, K.N.; Kim, H.K.

J. Microbiol. Biotechnol.

18

552-559

703230

-

Deactivation kinetics of nitrile hydratase in free resting cells

2009

Sun, X.; Yy, H.; Shen, Z.

Chin. J. Chem. Engin.

17

822-828

704051

19061912

The effects of acrylamide on brain creatine kinase: inhibition kinetics and computational docking simulation

2009

Lue, Z.R.; Zou, H.C.; Park, S.J.; Park, D.; Shi, L.; Oh, S.H.; Park, Y.D.; Bhak, J.; Zou, F.

Int. J. Biol. Macromol.

44

128-132

706832

20006698

Acrylamide catalytically inhibits topoisomerase II in V79 cells

2010

Sciandrello, G.; Mauro, M.; Caradonna, F.; Catanzaro, I.; Saverini, M.; Barbata, G.

Toxicol. In Vitro

24

830-834

711308

19819352

Structure and characterization of amidase from Rhodococcus sp. N-771: Insight into the molecular mechanism of substrate recognition

2010

Ohtaki, A.; Murata, K.; Sato, Y.; Noguchi, K.; Miyatake, H.; Dohmae, N.; Yamada, K.; Yohda, M.; Odaka, M.

Biochim. Biophys. Acta

1804

184-192

712726

20208436

Biotransformation of amides to acids using a co-cross-linked enzyme aggregate of Rhodococcus erythropolis amidase

2010

Park, H.J.; Uhm, K.N.; Kim, H.K.

J. Microbiol. Biotechnol.

20

325-331

712780

-

Cloning of amidase gene from Rhodococcus erythropolis and expression by distinct promoters in Bacillus subtilis

2009

Yue, Y.; Lian, J.; Tian, P.; Tan, T.

J. Mol. Catal. B

56

89-95

718459

-

New family of biuret hydrolases involved in s-triazine ring metabolism

2011

Cameron, S.; Durchschein, K.; Richman, J.; Sadowsky, M.; Wackett, L.

ACS Catal.

1

1075-1082

718531

-

Purification and characterization of amidase from acrylamide-degrading bacterium Burkholderia sp. strain DR.Y27

2012

Syed, M.; Ahmad, S.; Kusnin, N.; Shukor, M.

Afr. J. Biotechnol.

11

329-336

718672

22101784

Cloning and characterization of a novel amidase from Paracoccus sp. M-1, showing aryl acylamidase and acyl transferase activities

2012

Shen, W.; Chen, H.; Jia, K.; Ni, J.; Yan, X.; Li, S.

Appl. Microbiol. Biotechnol.

94

1007-1018

719432

11453462

Molecular and biochemical characterization of the recombinant amidase from hyperthermophilic archaeon Sulfolobus solfataricus

2001

dAbusco, A.S.; Ammendola, S.; Scandurra, R.; Politi, L.

Extremophiles

5

183-192

724942

24430467

Purification and characterization of a thermostable aliphatic amidase from the hyperthermophilic archaeon Pyrococcus yayanosii CH1

2014

Fu, L.; Li, X.; Xiao, X.; Xu, J.

Extremophiles

18

429-440

730077

24698299

Enhancement of thermo-stability and product tolerance of Pseudomonas putida nitrile hydratase by fusing with self-assembling peptide

2014

Liu, Y.; Cui, W.; Liu, Z.; Cui, Y.; Xia, Y.; Kobayashi, M.; Zhou, Z.

J. Biosci. Bioeng.

118

249-252

733127

23096998

Purification studies on a thermo-active amidase of Geobacillus pallidus BTP-5x MTCC 9225 isolated from thermal springs of Tatapani (Himachal Pradesh)

2013

Sharma, M.; Sharma, N.N.; Bhalla, T.C.

Appl. Biochem. Biotechnol.

169

1-14

753001

29486967

Promiscuous (+)-gamma-lactamase activity of an amidase from nitrile hydratase pathway for efficient synthesis of carbocyclic nucleosides intermediate

2018

Li, H.; Zhu, S.; Zheng, G.

Bioorg. Med. Chem. Lett.

28

1071-1076

755328

30097831

Expression and functional characterization of Pseudomonas aeruginosa recombinant L.asparaginase

2018

Saeed, H.; Soudan, H.; El-Sharkawy, A.; Farag, A.; Embaby, A.; Ataya, F.

Protein J.

37

461-471

757020

28959330

Production and characterization of a nitrilase from Pseudomonas aeruginosa RZ44 and its potential for nitrile biotransformation

2016

Badoei-Dalfard, A.; Ramezani-Pour, N.; Karami, Z.

Iran. J. Biotechnol.

14

142-153

Links to other databases for Acrylamide

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Show Links (1 entry)

ChEBI

PubChem

-