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Ligand 2-hydroxypropanoic acid

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

1.1.3.15

DL-lactate + O2 = pyruvate + H2O2

389691

-

1.1.3.15

lactate + O2 = pyruvate + H2O2

692867, 695773, 699088

-

1.3.1.110

lactate + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster = pyruvate + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster

731726

-

1.3.1.110

lactate + 2 NAD+ + 2 reduced ferredoxin [iron-sulfur] cluster = pyruvate + 2 NADH + 2 oxidized ferredoxin [iron-sulfur] cluster

763085

-

1.1.3.15

2 entries

1.3.1.110

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.4

DL-lactamide + H2O = DL-lactate + NH3

209125

-

3.8.1.2

2-chloropropionate + H2O = 2-hydroxypropionate + chloride

0

-

3.8.1.2

2-chloropropionate + H2O = lactate + HCl

0

-

3.8.1.2

2 entries

3.8.1.3

2-chloropropionate + H2O = 2-hydroxypropionate + chloride

0

-

4.1.2.36

formate + acetaldehyde = lactate

0

-

Substrate in Enzyme-catalyzed Reactions (22 results)

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Show Substrate (22 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.103

lactic acid + NAD+ = ?

738860

-

1.1.3.13

lactate + O2 = decanal + H2O2

740872

-

1.1.3.15

DL-lactate + O2 = pyruvate + H2O2

389691

-

1.1.3.15

lactate + O2 = pyruvate + H2O2

692867, 695773, 699088

-

1.1.3.15

2 entries

1.1.3.2

lactate + 2,6-dichlorophenolindophenol = ?

440395

-

1.1.99.14

DL-lactate + nitro blue tetrazolium = ? + reduced nitro blue tetrazolium

725738

-

1.1.99.30

lactate + oxidized acceptor = pyruvate + reduced acceptor

655314

-

1.11.1.13

NADH + lactate = NAD+ + ?

658297

-

1.12.2.1

lactate + ammonium pertechnetate = ?

686422

-

1.12.2.1

lactate + ferrocytochrome c3 = pyruvate + ferricytochrome c3

654261

-

1.12.2.1

2 entries

1.13.11.4

lactate + O2 = ?

658819

-

1.3.1.110

lactate + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster = pyruvate + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster

731726

-

1.3.1.110

lactate + 2 NAD+ + 2 reduced ferredoxin [iron-sulfur] cluster = pyruvate + 2 NADH + 2 oxidized ferredoxin [iron-sulfur] cluster

763085

-

1.3.1.110

2 entries

1.97.1.9

selenate + lactate = selenite + H2O + acetate + HCO3-

644812, 644813

-

2.8.3.1

acetyl-CoA + lactate = acetate + lactoyl-CoA

737535, 760715

-

2.8.3.1

acetyl-CoA + lactate = pyruvate + acetate + CoA

33928

-

2.8.3.1

lactate + acetyl-CoA = acetate + lactoyl-CoA

724088

-

3.4.13.18

lactate + L-isoleucine = N-L-lactoyl-L-isoleucine + H2O

755247

-

3.4.13.18

lactate + L-phenylalanine = N-L-lactoyl-L-phenylalanine + H2O

755247

-

3.4.13.18

lactate + L-tryptophan = N-L-lactoyl-L-tryptophan + H2O

755247

-

3.4.13.18

lactate + L-tyrosine = N-L-lactoyl-L-tyrosine + H2O

755247

-

2.8.3.1

3 entries

3.4.13.18

4 entries

6.2.1.B11

ATP + lactate + CoA = ADP + phosphate + lactoyl-CoA

725295

-

Product in Enzyme-catalyzed Reactions (41 results)

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Show Product (41 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.110

pyruvate + NAD(P)H + H+ = lactate + NAD(P)+

0

-

1.1.1.2

pyruvate + NADPH = 2-hydroxypropanoic acid + NADP+

0

-

1.1.1.215

pyruvate + NADPH + H+ = lactate + NADP+

286273

-

1.1.1.27

pyruvate + NADH + H+ = lactate + NAD+

0

-

1.1.1.337

glyoxylate + NADH + H+ = 2-hydroxypropanoate + NAD+

0

-

1.1.1.345

pyruvate + NADH + H+ = lactate + NAD+

0

-

1.1.1.37

pyruvate + NADH = 2-hydroxypropanoate + NAD+

0

-

1.1.1.428

pyruvate + NADH + H+ = lactate + NAD+

0

-

1.1.1.81

pyruvate + NADPH + H+ = lactate + NADP+

0

-

1.1.1.86

pyruvate + NADPH + H+ = 2-hydroxypropanoate + NADP+

0

-

1.1.99.30

pyruvate + reduced benzyl viologen = lactate + oxidized benzyl viologen

0

-

1.1.99.30

pyruvate + reduced methyl viologen = lactate + oxidized methyl viologen

0

-

1.1.99.30

2 entries

1.12.2.1

pyruvate + ferrocytochrome c3 = lactate + ferricytochrome c3

0

-

1.14.11.17

propionic acid + 2-oxoglutarate + O2 = 2-hydroxypropionic acid + succinate + CO2

0

-

1.3.1.110

pyruvate + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster = lactate + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster

0

-

3.1.1.13

p-nitrophenyllactate + H2O = p-nitrophenol + lactic acid

133840

-

3.1.2.12

S-lactoylglutathione + H2O = glutathione + lactate

0

-

3.1.2.7

S-lactoylglutathione + H2O = glutathione + lactate

81019

-

3.1.3.71

(R)-2-phospholactate + H2O = lactate + phosphate

0

-

3.1.3.71

(S)-2-phospholactate + H2O = lactate + phosphate

0

-

3.1.3.71

2 entries

3.5.1.124

N6-(1-hydroxy-2-oxopropyl)-[alpha-synuclein]-L-lysine + H2O = [alpha-synuclein]-L-lysine + lactate

0

-

3.5.1.4

DL-lactamide + H2O = DL-lactate + NH3

209125, 0

-

3.5.1.4

(R)-lactamide + H2O = lactate + NH3

0

-

3.5.1.4

(S)-lactamide + H2O = lactate + NH3

0

-

3.5.1.4

lactamide + H2O = lactate + NH3

0

-

3.5.1.4

R-lactamide + H2O = lactate + NH3

0

-

3.5.5.1

lactonitrile + H2O = lactate + NH3

209755

-

3.5.5.1

lactonitrile + H2O = lactic acid + NH3

0

-

3.5.1.4

5 entries

3.5.5.1

2 entries

3.8.1.10

DL-2-chloropropionate + H2O = DL-lactate + HCl

0

-

3.8.1.2

2-chloropropionate + H2O = 2-hydroxypropionate + chloride

0

-

3.8.1.2

DL-2-chloropropionate + H2O = DL-2-hydroxypropionate + chloride

0

-

3.8.1.2

2-chloropropionate + H2O = lactate + HCl

0

-

3.8.1.2

L-2-bromopropionate + H2O = lactate + HBr

0

-

3.8.1.2

L-2-chloropropionate + H2O = lactate + HCl

0

-

3.8.1.3

2-chloropropionate + H2O = 2-hydroxypropionate + chloride

0

-

3.8.1.3

2-fluoropropionic acid + H2O = 2-hydroxypropionate + fluoride

0

-

3.8.1.9

DL-2-bromopropionate + H2O = lactate + HBr

0

-

3.8.1.9

DL-2-chloropropionate + H2O = lactate + HCl

0

-

3.8.1.2

5 entries

3.8.1.3

2 entries

3.8.1.9

2 entries

4.1.1.101

DL-malate = DL-lactate + CO2

0

-

4.1.2.36

formate + acetaldehyde = lactate

0

-

5.3.3.2

pyruvate = lactate

0

-

Activator in Enzyme-catalyzed Reactions (13 results)

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Show Activating Compound (13 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.30

induces the enzyme when contained in the growth medium

656326

-

1.11.1.13

activates, chelates and stabilizes Mn3+

439842

-

1.11.1.13

activates, stabilizes Mn3+ in aqueous solution with a relatively high redox potential

439821, 439831

-

1.11.1.13

lactate serves as a chelator for the Mn3+ chelate formation, leading to a specific activity about 48.4% of that obtained with tartrate

699016

-

1.11.1.13

stimulates by complexing with and stabilizing Mn3+

439814, 439816, 439826, 439832

-

1.11.1.13

4 entries

1.14.11.2

stimulates, the activation of the enzyme in lactate-treated fibroblasts is correlated with a reduction in the total ADP-ribosylation

439190

-

2.7.11.11

increases intracellular cAMP, pCREB and PKA activity

723596

-

3.2.1.18

-

171130

-

3.4.22.56

induces the activation of caspase-3 in keratinocytes, the activation can be inhibited by N-carbobenzyloxy-VAD-fluoromethyl ketone, overview

699212

-

3.5.1.2

enhances activity

209028

-

3.5.3.7

5 mM, relative activity 106%

32148

-

5.6.1.2

2fold activation, maximum between 0.5 and 0.7 M

247027

-

6.4.1.1

activates

649374

-

Inhibitor in Enzyme-catalyzed Reactions (34 results)

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Show Inhibitors (34 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.153

0.03 mM, 20% inhibition

286013

-

1.1.1.153

20% inhibition of the reductive reaction at 0.03 mM

286013

-

1.1.1.153

2 entries

1.1.1.27

a high concentration of lactate has a weak inhibitory effect on the pyruvate reduction reaction activity but is meaningful for a significant lactate oxidation rate as the K m value of LDHA for L-lactate is very high

740458

-

1.1.1.30

5 mM, pH 8.5, 25°C, 65% inhibition

286524

-

1.1.1.30

-

669873

-

1.1.1.30

2 entries

1.1.1.39

-

286706

-

1.1.1.76

slight inhibition at 5 mM

389580

-

1.1.3.2

at concentrations higher than 20 mM

440395

-

1.1.3.2

growth rates of Streptococcus iniae expressing the type 2 enzyme are not reduced at lactate concentrations of 0.3% and 0.5%, whereas a strain expressing the type 1 enzyme exhibits reduced growth rates at these lactate concentrations

744092

-

1.1.3.2

2 entries

1.1.99.7

-

287849

-

1.14.11.2

less than 10% inhibition

439205

-

1.14.11.8

-

7020

-

1.14.18.1

3.73 mM, 50% inhibition of recombinant enzyme

636438

-

1.5.5.2

-

392560

-

1.5.99.B2

-

392568

-

1.5.99.B2

the activity is fully inhibited at 5 mM lactate

726429

-

1.5.99.B2

2 entries

2.4.2.19

1 mM, 29% inhibition

638028

-

2.7.1.1

lactate indirectly inhibits hexokinase activity, which results from its cellular redistribution, attributed to alterations of hexokinase structure. No modulation of hexokinase activity in heart or kidney

722275

-

2.7.1.11

-

702446

-

2.7.1.40

-

762099

-

2.7.3.2

induces dissociation of enzyme dimer and unfolding of the enzyme at 0.8 mM, but no aggregation at 25°C or 40°C even at high protein concentrations, inactivation kinetics

660930

-

3.2.1.2

complete inhibition at 10 mM, 58.3% inhibition at 1 mM

750376

-

3.2.1.23

noncompetitive

171302

-

3.5.1.1

about 70% inhibition at 10 mM

735144

-

3.5.1.14

-

288872, 288874

-

3.5.1.93

-

756424

-

4.1.1.1

-

114308

-

4.1.1.25

stronger inhibitory effect on strain ATCC 367 than on IOEB 9809

651348

-

4.1.1.64

-

4755

-

4.2.2.2

at 50 mM and above

666208

-

5.1.1.1

-

749379

-

5.3.2.2

-

2874

-

6.3.2.1

slight

978

-

6.3.2.1

-

978

-

6.3.2.1

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (26 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (26 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.27

2fn7, 3D-view

1.1.1.27

4jnk, 3D-view

1.1.1.27

4m49, 3D-view

1.1.1.27

4qo8, 3D-view

1.1.1.27

6baz, 3D-view

1.1.1.27

6bb0, 3D-view

1.1.1.27

6bb1, 3D-view

1.1.1.27

6bb2, 3D-view

1.1.1.27

6mv8, 3D-view

1.1.1.27

9 entries

1.1.1.28

3kb6, 3D-view

1.1.3.15

6m73, 3D-view

1.1.3.15

6m74, 3D-view

1.1.3.15

2 entries

1.13.11.54

5i8t, 3D-view

1.13.12.4

2nli, 3D-view

1.2.1.21

2imp, 3D-view

1.2.1.22

2imp, 3D-view

1.4.3.3

1c0k, 3D-view

2.4.1.217

2y4j, 3D-view

2.7.11.30

5s82, 3D-view

3.1.2.6

2p1e, 3D-view

3.2.2.22

4lwx, 3D-view

3.4.21.12

1p11, 3D-view

3.4.21.12

1p12, 3D-view

3.4.21.12

2 entries

3.5.1.124

5xr2, 3D-view

3.8.1.2

1qh9, 3D-view

4.1.3.3

2wnz, 3D-view

Enzyme Kinetic Parameters

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

1.1.1.27

3.3

-

-

696769

1.1.1.27

10.26

-

-

700558

1.1.1.27

47.4

-

LDHB, in the presence of 3.75 mM NAD+

697662

1.1.1.27

105.1

-

LDHB, in the presence of 3.75 mM NAD+

697662

1.1.1.27

4 entries

1.1.3.13

15.8

-

at pH 5.5 and 30°C

740872

1.1.3.15

27

-

-

389691

1.1.3.2

0.2

-

-

440395

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

1.1.1.30

0.9

-

-

669873

1.5.99.B2

0.9

-

-

392568

IC₅₀ Value (4 results)

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Show IC50 Value (4 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.7.1.40

34.4

-

muscle enzyme, pH 7.2, 22°C

762099

2.7.1.40

131

-

anoxic liver enzyme, pH 7.2, 22°C

762099

2.7.1.40

177.6

-

anoxic muscle enzyme, pH 7.2, 22°C

762099

2.7.1.40

187

-

liver enzyme, pH 7.2, 22°C

762099

2.7.1.40

4 entries

References & Links

Literature References (80)

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Show Reference (80 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

978

357689

Enzymological properties of pantothenate synthetase from Escherichia coli B

1978

Miyatake, K.; Nakano, Y.; Kitaoka, S.

J. Nutr. Sci. Vitaminol.

24

243-253

2874

5781999

Oxalacetate keto-enol tautomerase. Purification and characterization

1969

Annett, R.G.; Kosicki, G.W.

J. Biol. Chem.

244

2059-2067

4755

9521708

Pre-steady-state kinetic analysis of the reactions of alternate substrates with dialkylglycine decarboxylase

1998

Sun, S.; Bagdassarian, C.K.; Toney, M.D.

Biochemistry

37

3876-3885

7020

6813145

Mammalian enzymes of trimethyllysine conversion to trimethylaminobutyrate

1982

Henderson, L.M.; Nelson, P.J.; Henderson, L.

Fed. Proc.

41

2843-2847

32148

-

Characterization of 3-guanidinopropionate amidinohydrolase from Pseudomonas aeruginosa and a comparative study with 4-guanidinobutyrate amidinohydrolase from another Pseudomonas

1982

Yorifuji, T.; Sugai, I.; Matsumoto, H.; Tabuchi, A.

Agric. Biol. Chem.

46

1361-1367

33928

6586495

On the dehydration of (R)-lactate in the fermentation of alanine to propionate by Clostridium propionicum

1984

Schweiger, G.; Buckel, W.

FEBS Lett.

171

79-84

81019

-

Purification and characterization of glutathione thiol esterase from Saccharomyces cerevisiae

1987

Murata, K.; Sato, N.; Rhee, H.; Watanabe, K.; Kimura, A.

Agric. Biol. Chem.

51

1901-1907

114308

-

Isolation and characterization of maize pyruvate decarboxylase

1989

Leblova, S.; Malik, M.; Fojta, M.

Biologia (Bratisl. )

44

329-337

133840

7357021

Purification of rat liver lysosomal cholesteryl ester hydrolase

1980

Brown, W.J.; Sgoutas, D.S.

Biochim. Biophys. Acta

617

305-317

171130

6614909

Neuraminidase in Bacteroides fragilis

1983

Berg, J.O.; Lindqvist, L.; Andersson, G.; Nord, C.E.

Appl. Environ. Microbiol.

46

75-80

171302

6434507

Isolation and properties of beta-galactosidase of a strain of Lactobacillus helveticus isolated from natural whey starter

1983

Nadder de Macias, M.E.; Manca de Nadra, M.C.; Strasser de Saad, A.M.; Pesce de Ruiz Holgado, A.A.; Oliver, G.

J. Appl. Biochem.

5

275-281

209028

1546970

Glutamine catabolism by heart muscle. Properties of phosphate-activated glutaminase

1992

Nelson, D.; Rumsey, W.L.; Erecinska, M.

Biochem. J.

282

559-564

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

209755

-

Asymmetric hydrolysis of alpha-aminonitriles to optically active amino acids by a nitrilase of Rhodococcus rhodochrous PA-34

1992

Bhalla, T.C.; Miura, A.; Wakamoto, A.; Ohba, Y.; Furuhashi, K.

Appl. Microbiol. Biotechnol.

37

184-190

247027

2931437

Organic anions stabilize the reactivated motility of sperm flagella and the latency of dynein 1 ATPase activity

1985

Gibbons, B.H.; Tang, W.J.Y.; Gibbons, I.R.

J. Cell Biol.

101

1281-1287

286013

4401291

Sepiapterin reductase from horse liver: purification and properties of the enzyme

1971

Katoh, S.

Arch. Biochem. Biophys.

146

202-214

286273

-

Purification, crystallization and properties of 2-ketogluconate reductase from Acetobacter rancens

1976

Chiyonobu, T.; Shinagawa, E.; Adachi, O.; Ameyama, M.

Agric. Biol. Chem.

40

175-184

286524

-

Kinetics of D-3-hydroxybutyrate dehydrogenase from Paracoccus denitrificans

1986

Kovar, J.; Matyskova, I.; Matyska, L.

Biochim. Biophys. Acta

871

302-309

286706

10407149

Characterization of two members of a novel malic enzyme class

1999

Voegele, R.T.; Mitsch, M.J.; Finan, T.M.

Biochim. Biophys. Acta

1432

275-285

287849

4310090

Kinetics of malic-lactic transhydrogenase. Abortive complex formation with substrates and products

1969

Dolin, M.I.

J. Biol. Chem.

244

5273-5285

288872

-

Purification and characterization of L-aminoacylase from Pseudomonas maltophila B1

1998

Wakayama, M.; Shiiba, E.; Sakai, K.; Moriguchi, M.

J. Ferment. Bioeng.

85

278-282

288874

10898943

Noncompetitive, reversible inhibition of aminoacylase-1 by a series of L-alpha-hydroxyl and L-alpha-fluoro fatty acids: Ligand specificity of Aspergillus oryzae and porcine kindney enzymes

2000

Tamura, T.; Oki, Y.; Yoshida, A.; Kuriyama, T.; Kawakami, H.; Inoue, H.; Inagaki, K.; Tanaka, H.

Arch. Biochem. Biophys.

379

261-266

389580

11577733

Purification and characterization of L-2,3-butanediol dehydrogenase of Brevibacterium saccharolyticum C-1012 expressed in Escherichia coli

2001

Takusagawa, Y.; Otagiri, M.; Ui, S.; Ohtsuki, T.; Mimura, A.; Ohkuma, M.; Kudo, T.

Biosci. Biotechnol. Biochem.

65

1876-1878

389691

1148170

Rat kidney L-alpha-hydroxy acid oxidase: Isolation of enzyme with one flavine coenzyme per two subunits

1975

Cromartie, T.H.; Walsh, C.T.

Biochemistry

14

2588-2596

392560

355248

Membrane-bound proline dehydrogenase from Escherichia coli. Solubilization, purification, and characterization

1978

Scarpulla, R.C.; Soffer, R.L.

J. Biol. Chem.

253

5997-6001

392568

8373828

Mechanism-based inhibition of proline dehydrogenase by proline analogues

1993

Tritsch, D.; Mawlawi, H.; Biellmann, J.F.

Biochim. Biophys. Acta

1202

77-81

439190

2542248

Inhibition of prolyl hydroxylase by poly(ADP-ribose) and phosphoribosyl-AMP. Possible role of ADP-ribosylation in intracellular prolyl hydroxylase regulation

1989

Hussain, M.Z.; Ghani, Q.P.; Hunt, T.K.

J. Biol. Chem.

264

7850-7855

439205

200424

Mechanism of the prolyl hydroxylase reaction. 1. Role of co-substrates

1977

Tuderman, L.; Myllylä, R.; Kivirikko, K.I.

Eur. J. Biochem.

80

341-348

439814

3800395

Mn(II) oxidation is the principal function of the extracellular Mn-peroxidase from Phanerochaete chrysosporium

1986

Glenn, J.K.; Akileswaran, L.; Gold, M.H.

Arch. Biochem. Biophys.

251

688-696

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