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Ligand N-(3-oxododecanoyl)-L-homoserine lactone

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.81

N-3-oxo-dodecanoyl-L-homoserine lactone + H2O = N-3-oxo-dodecanoyl-L-homoserine

714534

-

3.1.1.81

N-3-oxododecanoyl-L-homoserine lactone + H2O = N-3-oxododecanoyl-L-homoserine

664956

-

3.5.1.97

N-3-oxo-dodecanoyl-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxododecanoate

756541, 757621

-

3.5.1.97

N-3-oxododecanoyl-(S)-homoserine lactone + H2O = (S)-homoserine + 3-oxododecanoic acid

665180

-

3.1.1.81

2 entries

3.5.1.97

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.184

3-oxododecanoyl-[acyl carrier protein] + S-adenosyl-L-methionine = N-(3-oxododecanoyl)-homoserine lactone + [acyl carrier protein] + 5'-methyl-thioadenosine

0

-

2.3.1.184

3-oxo-dodecanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = [acyl-carrier protein] + S-methyl-5'-thioadenosine + N-3-oxododecanoyl-L-homoserine lactone

0

-

2.3.1.184

3-oxododecanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = [acyl-carrier protein] + S-methyl-5'-thioadenosine + N-3-oxododecanoyl-L-homoserine lactone

0

-

2.3.1.184

S-adenosyl-L-methionine + 3-oxododecanoyl-[acyl-carrier protein] = 5'-methylthioadenosine + N-3-oxododecanoyl-L-homoserine-1,4-lactone + [acyl-carrier protein]

0

-

2.3.1.184

4 entries

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.25

N-(3-oxododecanoyl)-L-homoserine lactone + H2O = N-(3-oxododecanoyl)-L-homoserine

726350

-

3.1.1.81

3-oxo-dodecanoyl-L-homoserine lactone + H2O = 3-oxo-dodecanoyl-L-homoserine

752232

-

3.1.1.81

N-(3-oxo-dodecanoyl)-L-homoserine lactone + H2O = N-(3-oxo-dodecanoyl)-L-homoserine

731061

-

3.1.1.81

N-(3-oxododecanoyl)-L-homoserine lactone + H2O = N-(3-oxododecanoyl)-L-homoserine

749995, 751630, 715570, 686804, 724003

-

3.1.1.81

N-(3-oxododecyl)-L-homoserine lactone + H2O = N-(3-oxododecyl)-L-homoserine

729075

-

3.1.1.81

N-3-oxo-dodecanoyl-L-homoserine lactone + H2O = N-3-oxo-dodecanoyl-L-homoserine

714534, 715570

-

3.1.1.81

N-3-oxododecanoyl-L-homoserine lactone + H2O = N-3-oxododecanoyl-L-homoserine

664956, 750821, 665500, 752231, 666264, 752216, 749517, 752232, 749515, 750634, 751147, 749656, 750560, 666433, 751482

-

3.5.1.97

N-(3-oxododecanoyl)-L-homoserine lactone + H2O = ?

686804

-

3.5.1.97

N-(3-oxododecanoyl)-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxododecanoate

720390, 714841

-

3.5.1.97

N-3-oxo-dodecanoyl-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxododecanoate

756541, 757621, 755847

-

3.5.1.97

N-3-oxododecanoyl-(S)-homoserine lactone + H2O = (S)-homoserine + 3-oxododecanoic acid

665180

-

3.5.1.97

N-3-oxododecanoyl-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxododecanoic acid

750629, 710886, 750618

-

3.1.1.81

6 entries

3.5.1.97

5 entries

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.184

3-oxododecanoyl-[acyl carrier protein] + S-adenosyl-L-methionine = N-(3-oxododecanoyl)-homoserine lactone + [acyl carrier protein] + 5'-methyl-thioadenosine

0

-

2.3.1.184

3-oxododecanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = N-(3-oxododecanoyl)-L-homoserine lactone + [acyl-carrier protein] + S-methyl-5'-thioadenosine

0

-

2.3.1.184

3-oxo-dodecanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = [acyl-carrier protein] + S-methyl-5'-thioadenosine + N-3-oxododecanoyl-L-homoserine lactone

0

-

2.3.1.184

3-oxododecanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = [acyl-carrier protein] + S-methyl-5'-thioadenosine + N-3-oxododecanoyl-L-homoserine lactone

0

-

2.3.1.184

S-adenosyl-L-methionine + 3-oxododecanoyl-[acyl-carrier protein] = 5'-methylthioadenosine + N-3-oxododecanoyl-L-homoserine-1,4-lactone + [acyl-carrier protein]

0

-

2.3.1.184

5 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (17 results)

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Show Turnover Number (17 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.25

0.41

-

pH 8.3, 25°C, mutant enzyme W263F

726350

3.1.1.25

1.01

-

pH 8.3, 25°C, wild-type enzyme

726350

3.1.1.25

1.8

-

pH 8.3, 25°C, mutant enzyme W263I

726350

3.1.1.25

3

-

pH 8.3, 25°C, mutant enzyme W263V

726350

3.1.1.25

6.44

-

pH 8.3, 25°C, mutant enzyme W263T

726350

3.1.1.81

0.95

-

pH 8.0, 25°C

724003

3.1.1.81

1.83

-

pH 8.2, 25°C

729075

3.1.1.81

2

-

mutant enzyme E101G/R230C, in 2.5 mM Bicine buffer, pH 8.3, at 37°C

715570

3.1.1.81

2

-

pH 8.3, 37°C, recombinant mutant E101G/R230C

715570

3.1.1.81

4.9

-

in 2.5 mM Bicine pH 8.3, 150 mM NaCl, 0.2 mM cresol purple, 0.5% (v/v) DMSO and 0.2 mM CoCl2, at 25°C

752232

3.1.1.81

4.9

-

pH 8.3, 25°C

752232

3.1.1.81

5.03

-

pH 8.3, 25°C

749517

3.1.1.81

6.9

-

mutant enzyme E101N/R230I, in 2.5 mM Bicine buffer, pH 8.3, at 37°C

715570

3.1.1.81

6.9

-

pH 8.3, 37°C, recombinant mutant E101N/R230I

715570

3.1.1.81

9.48

-

pH 8.3, 25°C

749515

3.1.1.81

101.5

-

pH 7.2, 30°C

750560

3.1.1.81

224

-

pH 7.1, 25°C

749656

3.1.1.25

5 entries

3.1.1.81

12 entries

K_M Value (18 results)

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Show KM Value (18 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.25

0.0178

-

pH 8.3, 25°C, mutant enzyme W263I

726350

3.1.1.25

0.0247

-

pH 8.3, 25°C, mutant enzyme W263V

726350

3.1.1.25

0.137

-

pH 8.3, 25°C, mutant enzyme W263T

726350

3.1.1.25

0.146

-

pH 8.3, 25°C, mutant enzyme W263F

726350

3.1.1.25

0.456

-

pH 8.3, 25°C, wild-type enzyme

726350

3.1.1.81

0.00219

-

pH 8.3, 25°C

749515

3.1.1.81

0.014

-

pH 8.3, 25°C

749517

3.1.1.81

0.0174

-

in 2.5 mM Bicine pH 8.3, 150 mM NaCl, 0.2 mM cresol purple, 0.5% (v/v) DMSO and 0.2 mM CoCl2, at 25°C

752232

3.1.1.81

0.0174

-

pH 8.3, 25°C

752232

3.1.1.81

0.101

-

pH 8.0, 22°C, recombinant enzyme

749995

3.1.1.81

0.101

-

pH 8.2, 25°C

729075

3.1.1.81

0.17

-

pH 8.0, 25°C

724003

3.1.1.81

0.44

-

pH 7.1, 25°C

749656

3.1.1.81

0.48

-

mutant enzyme E101G/R230C, in 2.5 mM Bicine buffer, pH 8.3, at 37°C

715570

3.1.1.81

0.48

-

pH 8.3, 37°C, recombinant mutant E101G/R230C

715570

3.1.1.81

0.74

-

mutant enzyme E101N/R230I, in 2.5 mM Bicine buffer, pH 8.3, at 37°C

715570

3.1.1.81

0.74

-

pH 8.3, 37°C, recombinant mutant E101N/R230I

715570

3.1.1.81

15.21

-

pH 7.2, 30°C

750560

3.1.1.25

5 entries

3.1.1.81

13 entries

References & Links

Literature References (33)

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Show Reference (33 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

664956

15963993

Quorum quenching enzyme activity is widely conserved in the sera of mammalian species

2005

Yang, F.; Wang, L.H.; Wang, J.; Dong, Y.H.; Hu, J.Y.; Zhang, L.H.

FEBS Lett.

579

3713-3717

665180

16495538

Quorum quenching by an N-acyl-homoserine lactone acylase from Pseudomonas aeruginosa PAO1

2006

Sio, C.F.; Otten, L.G.; Cool, R.H.; Diggle, S.P.; Braun, P.G.; Bos, R.; Daykin, M.; Camara, M.; Williams, P.; Quax, W.J.

Infect. Immun.

74

1673-1682

665500

14734559

Specificity and enzyme kinetics of the quorum-quenching N-acyl homoserine lactone lactonase (AHL-lactonase)

2004

Wang, L.H.; Weng, L.X.; Dong, Y.H.; Zhang, L.H.

J. Biol. Chem.

279

13645-13651

666264

12777494

AhlD, an N-acylhomoserine lactonase in Arthrobacter sp., and predicted homologues in other bacteria

2003

Park, S.Y.; Lee, S.J.; Oh, T.K.; Oh, J.W.; Koo, B.T.; Yum, D.Y.; Lee, J.K.

Microbiology

149

1541-1550

666433

11459062

Quenching quorum-sensing-dependent bacterial infection by an N-acyl homoserine lactonase

2001

Dong, Y.H.; Wang, L.H.; Xu, J.L.; Zhang, H.B.; Zhang, X.F.; Zhang, L.H.

Nature

411

813-817

686804

18194337

Quorum quenching activity in Anabaena sp. PCC 7120: identification of AiiC, a novel AHL-acylase

2008

Romero, M.; Diggle, S.P.; Heeb, S.; Camara, M.; Otero, A.

FEMS Microbiol. Lett.

280

73-80

710886

19721066

Quorum-quenching acylase reduces the virulence of Pseudomonas aeruginosa in a Caenorhabditis elegans infection model

2009

Papaioannou, E.; Wahjudi, M.; Nadal-Jimenez, P.; Koch, G.; Setroikromo, R.; Quax, W.J.

Antimicrob. Agents Chemother.

53

4891-4897

714534

21897031

Isolation and characterization of N-acylhomoserine lactonase from the Thermophilic bacterium, Geobacillus caldoxylosilyticus YS-8

2011

Seo, M.J.; Lee, B.S.; Pyun, Y.R.; Park, H.

Biosci. Biotechnol. Biochem.

75

1789-1795

714841

23761232

Inactivation of AHLs by Ochrobactrum sp. A44 depends on the activity of a novel class of AHL acylase

2011

Czajkowski, R.; Krzyzanowska, D.; Karczewska, J.; Atkinson, S.; Przysowa, J.; Lojkowska, E.; Williams, P.; Jafra, S.

Environ. Microbiol. Rep.

3

59-68

715570

20980257

Directed evolution of a thermostable quorum-quenching lactonase from the amidohydrolase superfamily

2010

Chow, J.Y.; Xue, B.; Lee, K.H.; Tung, A.; Wu, L.; Robinson, R.C.; Yew, W.S.

J. Biol. Chem.

285

40911-40920

720390

21372094

PA0305 of Pseudomonas aeruginosa is a quorum quenching acylhomoserine lactone acylase belonging to the Ntn hydrolase superfamily

2011

Wahjudi, M.; Papaioannou, E.; Hendrawati, O.; van Assen, A.H.; van Merkerk, R.; Cool, R.H.; Poelarends, G.J.; Quax, W.J.

Microbiology

157

2042-2055

724003

21183649

Characterization of a phosphotriesterase-like lactonase from Sulfolobus solfataricus and its immobilization for disruption of quorum sensing

2010

Ng, F.S.; Wright, D.M.; Seah, S.Y.

Appl. Environ. Microbiol.

77

1181-1186

726350

24086491

Differential active site loop conformations mediate promiscuous activities in the lactonase SsoPox

2013

Hiblot, J.; Gotthard, G.; Elias, M.; Chabriere, E.

PLoS One

8

e75272

729075

24057406

Rhodococcus lactonase with organophosphate hydrolase (OPH) activity and His6-tagged OPH with lactonase activity: evolutionary proximity of the enzymes and new possibilities in their application

2014

Sirotkina, M.; Efremenko, E.N.

Appl. Microbiol. Biotechnol.

98

2647-2656

731061

23275166

High-resolution structures of AidH complexes provide insights into a novel catalytic mechanism for N-acyl homoserine lactonase

2013

Gao, A.; Mei, G.Y.; Liu, S.; Wang, P.; Tang, Q.; Liu, Y.P.; Wen, H.; An, X.M.; Zhang, L.Q.; Yan, X.X.; Liang, D.C.

Acta Crystallogr. Sect. D

69

82-91

749515

27599858

The quorum-quenching lactonase from Geobacillus caldoxylosilyticus purification, characterization, crystallization and crystallographic analysis

2016

Bergonzi, C.; Schwab, M.; Elias, M.

Acta Crystallogr. Sect. F

72

681-686

749517

28777091

The quorum-quenching lactonase from Alicyclobacter acidoterrestris purification, kinetic characterization, crystallization and crystallographic analysis

2017

Bergonzi, C.; Schwab, M.; Chabriere, E.; Elias, M.

Acta Crystallogr. Sect. F

73

476-480

749656

25398866

MomL, a novel marine-derived N-Acyl homoserine lactonase from Muricauda olearia

2015

Tang, K.; Su, Y.; Brackman, G.; Cui, F.; Zhang, Y.; Shi, X.; Coenye, T.; Zhang, X.

Appl. Environ. Microbiol.

81

774-782

749995

29870390

Novel approach to quorum quenching rational design of antibacterials in combination with hexahistidine-tagged organophosphorus hydrolase

2018

Aslanli, A.; Lyagin, I.; Efremenko, E.

Biol. Chem.

399

869-879

750560

29518220

Purification and characterisation of a quorum quenching AHL-lactonase from the endophytic bacterium Enterobacter sp. CS66

2018

Shastry, R.P.; Dolan, S.K.; Abdelhamid, Y.; Vittal, R.R.; Welch, M.

FEMS Microbiol. Lett.

365

fny054

750618

29755959

PvdQ quorum quenching acylase attenuates Pseudomonas aeruginosa virulence in a mouse model of pulmonary infection

2018

Utari, P.; Setroikromo, R.; Melgert, B.; Quax, W.

Front. Cell. Infect. Microbiol.

8

119

750629

28674525

Deciphering physiological functions of AHL quorum quenching acylases

2017

Utari, P.; Vogel, J.; Quax, W.

Front. Microbiol.

8

1123

750634

29067011

Aii810, a novel cold-adapted N-acylhomoserine lactonase discovered in a metagenome, can strongly attenuate Pseudomonas aeruginosa virulence factors and biofilm formation

2017

Fan, X.; Liang, M.; Wang, L.; Chen, R.; Li, H.; Liu, X.

Front. Microbiol.

8

1950

750821

26432367

Purification and antibiofilm activity of AHL-lactonase from endophytic Enterobacter aerogenes VT66

2015

Rajesh, P.S.; Rai, V.R.

Int. J. Biol. Macromol.

81

1046-1052

751147

30391237

Distribution and characterization of N-acylhomoserine lactone (AHL)-degrading activity and AHL lactonase gene (qsdS) in Sphingopyxis

2018

Morohoshi, T.; Kamimura, Y.; Sato, N.; Iizumi, T.

J. Biosci. Bioeng.

127

411-417

751482

30445965

Characterization of a novel N-acylhomoserine lactonase, AidP, from Antarctic Planococcus sp

2018

See-Too, W.S.; Convey, P.; Pearce, D.A.; Chan, K.G.

Microb. Cell Fact.

17

179

751630

29415497

Modification and assembly of a versatile lactonase for bacterial quorum quenching

2018

Rhoads, M.K.; Hauk, P.; Gupta, V.; Bookstaver, M.L.; Stephens, K.; Payne, G.F.; Bentley, W.E.

Molecules

23

E341

752216

29196634

Rational engineering of a native hyperthermostable lactonase into a broad spectrum phosphotriesterase

2017

Jacquet, P.; Hiblot, J.; Daude, D.; Bergonzi, C.; Gotthard, G.; Armstrong, N.; Chabriere, E.; Elias, M.

Sci. Rep.

7

16745

752231

28424524

HqiA, a novel quorum-quenching enzyme which expands the AHL lactonase family

2017

Torres, M.; Uroz, S.; Salto, R.; Fauchery, L.; Quesada, E.; Llamas, I.

Sci. Rep.

7

943

752232

30050039

Structural and biochemical characterization of AaL, a quorum quenching lactonase with unusual kinetic properties

2018

Bergonzi, C.; Schwab, M.; Naik, T.; Daude, D.; Chabriere, E.; Elias, M.

Sci. Rep.

8

11262

755847

28455333

A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance

2017

Kusada, H.; Tamaki, H.; Kamagata, Y.; Hanada, S.; Kimura, N.

Appl. Environ. Microbiol.

83

e00080-17

756541

31292680

Quorum quenching enzyme APTM01, an acylhomoserine-lactone acylase from marine bacterium of Pseudoalteromonas tetraodonis strain MQS005

2019

Pan, Y.; Wang, Y.; Yan, X.; Liu, C.; Wu, B.; He, X.; Liang, Y.

Curr. Microbiol.

76

1387-1397

757621

28920855

PfmA, a novel quorum-quenching N-acylhomoserine lactone acylase from Pseudoalteromonas flavipulchra

2017

Liu, N.; Yu, M.; Zhao, Y.; Cheng, J.; An, K.; Zhang, X.H.

Microbiology

163

1389-1398

Links to other databases for N-(3-oxododecanoyl)-L-homoserine lactone

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PubChem