print visible entries

print all entries

Ligand 3-fluorobenzoate

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (7 results)

top print hide

Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.12.10

3-fluorobenzoate + O2 + NADH + H+ = 3-fluoro-2-hydro-1,2-dihydroxybenzoate + NAD+

396142, 396138

-

1.14.13.24

3-fluorobenzoate + NAD(P)H + O2 = ?

674255

-

1.14.14.92

3-fluorobenzoate + [reduced NADPH-hemoprotein reductase] + O2 = 3-fluoro-4-hydroxybenzoate + [oxidized NADPH-hemoprotein reductase] + H2O

440261

-

1.2.99.6

3-Fluorobenzoate + reduced carbamoyl methyl viologen = 3-Fluorobenzaldehyde + carbamoyl methyl viologen

11939, 11943

-

6.2.1.25

ATP + 3-fluorobenzoate + CoA = AMP + diphosphate + 3-fluorobenzoyl-CoA

715, 744341, 708, 709, 713, 711, 651721, 662906, 662016, 673729, 675454

-

6.2.1.32

ATP + 3-fluorobenzoate + CoA = AMP + 3-fluorobenzoyl-CoA + diphosphate

713

-

6.2.1.71

ATP + 3-fluorobenzoate = diphosphate + (3-fluorobenzoyl)adenylate

760609

-

Product in Enzyme-catalyzed Reactions (8 results)

top print hide

Show Product (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.3.7

3-fluorobenzaldehyde + O2 = 3-fluorobenzoic acid + H2O2

0

-

1.2.1.28

3-fluorobenzaldehyde + NAD+ + H2O = 3-fluorobenzoate + NADH + H+

390225, 389587, 390228

-

1.2.1.3

m-fluorobenzaldehyde + NAD+ + H2O = m-fluorobenzoic acid + NADH + H+

0

-

1.2.1.32

3-fluorobenzaldehyde + NAD+ + H2O = 3-fluorobenzoate + NADH + H+

0

-

1.2.1.48

m-fluorobenzaldehyde + NAD+ + H2O = m-fluorobenzoic acid + NADH + H+

390325

-

1.2.1.5

m-fluorobenzaldehyde + NAD(P)+ + H2O = m-fluorobenzoate + NAD(P)H + H+

0

-

1.2.1.85

3-fluorobenzaldehyde + NAD+ + H2O = 3-fluorobenzoate + NADH + H+

0

-

3.5.5.1

3-fluorobenzonitrile + H2O = 3-fluorobenzoic acid + NH3

209762, 209761, 209746

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.2

-

391799

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

top print hide

Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.92

4.83

-

-

440261

6.2.1.25

35

-

pH 8.0, 31°C, recombinant wild-type enzyme

744341

K_M Value (3 results)

top print hide

Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.92

0.086

-

-

440261

1.2.99.6

3.5

-

with reduced carbamoyl methyl viologen as cosubstrate

11939

6.2.1.25

0.073

-

pH 8.0, 31°C, recombinant wild-type enzyme

744341

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.4.3.2

0.37

-

-

391799

References & Links

Literature References (26)

top print hide

Show Reference (26 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

708

2857161

Anaerobic degradation of 2-fluorobenzoate by benzoate-degrading, denitrifying bacteria

1985

Schennen, U.; Braun, K.; Knackmuss, H.J.

J. Bacteriol.

161

321-325

709

-

Activation of aromatic acids and aerobic 2-aminobenzoate metabolism in a denitrifying Pseudomonas strain

1989

Ziegler, K.; Buder, R.; Winter, J.; Fuchs, G.

Arch. Microbiol.

151

171-176

711

1369492

Purification and chracterization of benzoyl-CoA ligase from a syntrophic, benzoate-degrading, anaerobic mixed culture

1992

Auburger, G.; Winter, J.

Appl. Microbiol. Biotechnol.

37

789-795

713

1885526

Purification and characterization of benzoate-coenzyme A ligase and 2-aminobenzoate-coenzyme A ligase from a denitrifying Pseudomonas sp.

1991

Altenschmidt, U.; Oswald, B.; Fuchs, G.

J. Bacteriol.

173

5494-5501

715

8335640

New aerobic benzoate oxidation pathway via benzoyl-coenzyme A and 3-hydroxybenzoyl-coenzyme A in a denitrifying Pseudomonas sp.

1993

Altenschmidt, U.; Oswald, B.; Steiner, E.; Herrmann, H.; Fuchs, G.

J. Bacteriol.

175

4851-4858

11939

-

Pterin cofactor, substrate specificity, and observations on the kinetics of the reversible tungsten-containing aldehyde oxidoreductase from Clostridium thermoaceticum

1995

Huber, C.; Skopan, H.; Feicht, R.; White, H.; Simon, H.

Arch. Microbiol.

164

110-118

11943

1793519

Purification and some properties of the tungsten-containing carboxylic acid reductase from Clostridium formicoaceticum

1991

White, H.; Feicht, R.; Huber, C.; Lottspeich, F.; Simon, H.

Biol. Chem. Hoppe-Seyler

372

999-1005

209746

10591020

Characterization of an inducible nitrilase from a thermophilic bacillus

1999

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

Extremophiles

3

283-291

209761

23761

Fungal degradation of aromatic nitriles. Enzymology of C-N cleavage by Fusarium solani

1977

Harper, D.B.

Biochem. J.

167

685-692

209762

21655

Microbial metabolism of aromatic nitriles. Enzymology of C-N cleavage by Nocardia sp. (Rhodococcus group) N.C.I.B. 11216

1977

Harper, D.B.

Biochem. J.

165

309-319

389587

3060114

Benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase II from Acinetobacter calcoaceticus. Substrate specificities and inhibition studies

1988

MacKintosh, R.W.; Fewson, C.A.

Biochem. J.

255

653-661

390225

7868591

Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida

1995

Inoue, J.; Shaw, J.P.; Rekik, M.; Harayama, S.

J. Bacteriol.

177

1196-1201

390228

2597133

Purification and characterization of benzaldehyde dehydrogenase I from Acinetobacter calcoaceticus [published erratum appears in Biochem J 1990 Feb 1;265(6):931]

1989

Chalmers, R.M.; Fewson, C.A.

Biochem. J.

263

913-919

390325

10919810

Long-chain aldehyde dehydrogenase that participates in n-alkane utilization and wax ester synthesis in Acinetobacter sp. strain M-1

2000

Ishige, T.; Tani, A.; Sakai, Y.; Kato, N.

Appl. Environ. Microbiol.

66

3481-3486

391799

5693709

Studies on L-amino-acid oxidase. I. Effects of pH and competitive inhibitors

1968

De Kok, A.; Veeger, C.

Biochim. Biophys. Acta

167

35-47

396138

7372624

Purification and characterization of an oxygenase component in benzoate 1,2-dioxygenase system from Pseudomonas arvilla C-1

1980

Yamaguchi, M.; Fujisawa, H.

J. Biol. Chem.

255

5058-5063

396142

12135383

Benzoate 1,2-dioxygenase from Pseudomonas putida: single turnover kinetics and regulation of a two-component Rieske dioxygenase

2002

Wolfe, M.D.; Altier, D.J.; Stubna, A.; Popescu, C.V.; Muenck, E.; Lipscomb, J.D.

Biochemistry

41

9611-9626

440261

11594739

Purification and characterization of benzoate-para-hydroxylase, a cytochrome P450 (CYP53A1), from Aspergillus niger

2001

Faber, B.W.; van Gorcom, R.F.; Duine, J.A.

Arch. Biochem. Biophys.

394

245-254

651721

12897012

Benzoate-coenzyme A ligase from Thauera aromatica: an enzyme acting in anaerobic and aerobic pathways

2003

Schuhle, K.; Gescher, J.; Feil, U.; Paul, M.; Jahn, M.; Schagger, H.; Fuchs, G.

J. Bacteriol.

185

4920-4929

662016

15317781

The bzd gene cluster, coding for anaerobic benzoate catabolism, in Azoarcus sp. strain CIB

2004

Lopez Barragan, M.J.; Carmona, M.; Zamarro, M.T.; Thiele, B.; Boll, M.; Fuchs, G.; Garcia, J.L.; Diaz, E.

J. Bacteriol.

186

5762-5774

662906

16313613

Gene clusters involved in anaerobic benzoate degradation of Geobacter metallireducens

2005

Wischgoll, S.; Heintz, D.; Peters, F.; Erxleben, A.; Sarnighausen, E.; Reski, R.; Van Dorsselaer, A.; Boll, M.

Mol. Microbiol.

58

1238-1252

673729

16553855

Purification and characterization of benzoate-CoA ligase from Magnetospirillum sp. strain TS-6 capable of aerobic and anaerobic degradation of aromatic compounds

2006

Kawaguchi, K.; Shinoda, Y.; Yurimoto, H.; Sakai, Y.; Kato, N.

FEMS Microbiol. Lett.

257

208-213

674255

16267294

Molecular and biochemical characterization of the xlnD-encoded 3-hydroxybenzoate 6-hydroxylase involved in the degradation of 2,5-xylenol via the gentisate pathway in Pseudomonas alcaligenes NCIMB 9867

2005

Gao, X.; Tan, C.L.; Yeo, C.C.; Poh, C.L.

J. Bacteriol.

187

7696-7702

675454

17884091

Biochemical and structural characterization of the paralogous benzoate CoA ligases from Burkholderia xenovorans LB400: defining the entry point into the novel benzoate oxidation (box) pathway

2007

Bains, J.; Boulanger, M.J.

J. Mol. Biol.

373

965-977

744341

26378464

Kinetically and crystallographically guided mutations of a benzoate CoA ligase (BadA) elucidate mechanism and expand substrate permissivity

2015

Thornburg, C.K.; Wortas-Strom, S.; Nosrati, M.; Geiger, J.H.; Walker, K.D.

Biochemistry

54

6230-6242

760609

31894971

Precise probing of residue roles by NRPS code swapping mutation, enzymatic characterization, modeling, and substrate promiscuity of aryl acid adenylation domains

2020

Ishikawa, F.; Nohara, M.; Nakamura, S.; Nakanishi, I.; Tanabe, G.

Biochemistry

59

351-363

Links to other databases for 3-fluorobenzoate

top print hide

Show Links (1 entry)

ChEBI

PubChem