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Ligand 2-dehydro-3-deoxy-D-gluconate

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

degradation of sugar acids, Entner Doudoroff pathway

KEGG

Carbon metabolism, Microbial metabolism in diverse environments, Pentose and glucuronate interconversions, Pentose phosphate pathway

MetaCyc

3,6-anhydro-alpha-L-galactopyranose degradation, 4-deoxy-L-threo-hex-4-enopyranuronate degradation, alginate degradation, D-fructuronate degradation, D-galactarate degradation I, D-galactarate degradation II, D-galacturonate degradation I, D-galacturonate degradation II, D-glucarate degradation I, D-glucarate degradation II, D-glucuronate degradation II, Entner-Doudoroff pathway II (non-phosphorylative), Entner-Doudoroff pathway III (semi-phosphorylative) more

Show all BRENDA pathways known for 2-dehydro-3-deoxy-D-gluconate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Natural Substrate (12 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

2-dehydro-3-deoxy-D-gluconate + NADH + H+ = 4-deoxy-L-erythro-5-hexoseulose + NAD+

745695

-

1.1.1.126

2-dehydro-3-deoxy-D-gluconate + NAD+ = (4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + NADH + H+

739788

-

1.1.1.127

2-dehydro-3-deoxy-D-gluconate + NAD+ = (4S)-4,6-dihydroxy-2,5-dioxohexanoate + NADH

285821, 285820

-

2.7.1.11

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

738267

-

2.7.1.178

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

722247, 738267, 737511

-

2.7.1.178

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

719488, 672669, 722247

-

2.7.1.45

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

738267, 759703

-

2.7.1.45

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

657469, 636961

-

2.7.1.178

2 entries

2.7.1.45

2 entries

4.1.2.14

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

695041

-

4.1.2.21

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

695041

-

4.1.2.51

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

704334

-

4.1.2.55

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

747152, 719488, 657872, 656156

-

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

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Show Natural Product (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

4-deoxy-L-erythro-5-hexoseulose + NAD+ = 2-dehydro-3-deoxy-D-gluconate + NADH + H+

-

-

1.1.1.126

(4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + NADPH = 2-dehydro-3-deoxy-D-gluconate + NADP+

285819

-

1.1.1.127

2,5-didehydro-3-deoxy-D-gluconate + NADH + H+ = 2-dehydro-3-deoxy-D-gluconate + NAD+

-

-

1.1.1.127

2,5-didehydro-3-deoxy-D-gluconate + NADPH + H+ = 2-dehydro-3-deoxy-D-gluconate + NADP+

-

-

1.1.1.127

2 entries

1.2.1.23

2-dehydro-3-deoxy-D-glucose + NAD+ + H2O = 2-dehydro-3-deoxy-D-gluconate + NADH + H+

288145, 288147

-

1.2.1.49

2-keto-3-deoxy-D-glucose + NADP+ + H2O = 2-keto-3-deoxy-D-gluconic acid + NADPH + H+

288145

-

4.2.1.140

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.39

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

Substrate in Enzyme-catalyzed Reactions (23 results)

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Show Substrate (23 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

2-dehydro-3-deoxy-D-gluconate + NADH + H+ = 4-deoxy-L-erythro-5-hexoseulose + NAD+

745695

-

1.1.1.126

2-dehydro-3-deoxy-D-gluconate + NAD+ = (4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + NADH + H+

739788

-

1.1.1.127

2-dehydro-3-deoxy-D-gluconate + NAD+ = (4S)-4,6-dihydroxy-2,5-dioxohexanoate + NADH

285821, 285820

-

2.7.1.11

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

738267

-

2.7.1.13

ATP + 2-keto-3-deoxy-D-gluconate = ADP + ?

759808

-

2.7.1.178

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

722247, 738267, 737511

-

2.7.1.178

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

722247, 672669, 719488

-

2.7.1.45

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

738267, 759808, 759703

-

2.7.1.45

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

657469, 636960, 636961, 672718, 676988, 659714

-

2.7.1.45

CTP + 2-dehydro-3-deoxy-D-gluconate = CDP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

636960

-

2.7.1.45

GTP + 2-dehydro-3-deoxy-D-gluconate = GDP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

636960, 676988

-

2.7.1.45

ITP + 2-dehydro-3-deoxy-D-gluconate = IDP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

636960, 676988

-

2.7.1.45

TTP + 2-dehydro-3-deoxy-D-gluconate = TDP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

676988

-

2.7.1.45

UTP + 2-dehydro-3-deoxy-D-gluconate = UDP + 6-phospho-2-dehydro-3-deoxy-D-gluconate

636960

-

2.7.1.178

2 entries

2.7.1.45

7 entries

2.7.1.58

ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 2-dehydro-3-deoxy-6-phospho-D-gluconate

759203

-

4.1.2.14

2-dehydro-3-deoxy-D-gluconate = ?

682736

-

4.1.2.14

2-dehydro-3-deoxy-D-gluconate = pyruvate + ?

747152

-

4.1.2.14

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

650823, 665573, 695041, 748105

-

4.1.2.14

D-2-dehydro-3-deoxygluconate = pyruvate + D-glyceraldehyde

650823

-

4.1.2.14

4 entries

4.1.2.20

2-dehydro-3-deoxy-D-gluconate = pyruvate + glyceraldehyde

704334

-

4.1.2.21

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

695041

-

4.1.2.51

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

704334

-

4.1.2.55

2-dehydro-3-deoxy-D-gluconate = pyruvate + D-glyceraldehyde

722059, 747152, 719488, 657872, 656156, 665573

-

Product in Enzyme-catalyzed Reactions (25 results)

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Show Product (25 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

4-deoxy-L-erythro-5-hexoseulose + NAD+ = 2-dehydro-3-deoxy-D-gluconate + NADH + H+

-

-

1.1.1.126

(4S,5S)-4,5-dihydroxy-2,6-dioxohexanoate + NADPH = 2-dehydro-3-deoxy-D-gluconate + NADP+

285819

-

1.1.1.127

2,5-didehydro-3-deoxy-D-gluconate + NADH + H+ = 2-dehydro-3-deoxy-D-gluconate + NAD+

-

-

1.1.1.127

2,5-didehydro-3-deoxy-D-gluconate + NADPH + H+ = 2-dehydro-3-deoxy-D-gluconate + NADP+

-

-

1.1.1.127

2 entries

1.2.1.23

2-dehydro-3-deoxy-D-glucose + NAD+ + H2O = 2-dehydro-3-deoxy-D-gluconate + NADH + H+

288145, 288147

-

1.2.1.36

3-deoxyglucosone + NAD+ + H2O = 2-keto-3-deoxygluconate + NADH + H+

-

-

1.2.1.49

2-keto-3-deoxy-D-glucose + NADP+ + H2O = 2-keto-3-deoxy-D-gluconate + NADPH + H+

-

-

1.2.1.49

2-keto-3-deoxy-D-glucose + NADP+ + H2O = 2-keto-3-deoxy-D-gluconic acid + NADPH + H+

288145

-

4.1.2.14

pyruvate + D-glyceraldehyde = 2-dehydro-3-deoxy-D-gluconate

653924,

-

4.1.2.14

pyruvate + DL-glyceraldehyde 3-phosphate = 2-dehydro-3-deoxy-D-gluconate

650823

-

4.1.2.55

pyruvate + D-glyceraldehyde = 2-dehydro-3-deoxy-D-gluconate

-

-

4.1.2.55

pyruvate + D-glyceraldehyde = 3-deoxy-D-erythro-hex-2-ulosonate

-

-

4.1.2.55

pyruvate + L-glyceraldehyde = 3-deoxy-D-erythro-hex-2-ulosonate

-

-

1.2.1.49

2 entries

4.1.2.14

2 entries

4.1.2.55

3 entries

4.2.1.140

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.39

D-gluconate = 2-dehydro-3-deoxy-D-gluconate

-

-

4.2.1.39

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.39

gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.39

3 entries

4.2.1.68

D-mannonate = 2-dehydro-3-deoxy-D-mannonate + H2O

-

-

4.2.1.7

D-altronate = 2-dehydro-3-deoxy-D-gluconate + H2O

5900,

-

4.2.1.8

D-Mannonate = 2-Dehydro-3-deoxy-D-gluconate + H2O

5899, 5900, 5901, 5903, 5902,

4kpl, 3D-view

4.2.1.82

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.9

D-gluconate = 2-dehydro-3-deoxy-D-gluconate + H2O

-

-

4.2.1.9

D-gluconate = 2-keto-3-deoxygluconate + H2O

-

-

4.3.1.9

D-glucosaminate = 2-dehydro-3-deoxy-D-gluconate

, 644483, 644481

-

4.3.1.9

D-glucosaminate = 2-dehydro-3-deoxy-D-gluconate + NH3

650409

-

4.2.1.9

2 entries

4.3.1.9

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

4.1.2.14

-

4971

-

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (2 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.7.1.4

2var, 3D-view

4.2.1.8

4kpl, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (28 results)

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Show Turnover Number (28 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.1

1.4

-

at pH 7.9 and 25°C

745695

2.7.1.13

10.2

-

pH 8.0, temperature not specified in the publication

759808

2.7.1.178

5

-

pH 7.5, 60°C

719488

2.7.1.178

60.8

-

pH 7.2, 60°C

672669

2.7.1.45

8.26

-

in 50 mM Tris/HCl (pH 8.5) at 50°C

676988

2.7.1.45

8.26

-

pH 8.5, 50°C

676988

2.7.1.45

11

-

pH 7.4, 35°C, in presence of 5 mM MgCl2 and 0.1 M KCl

659714

4.1.2.14

0.016

-

wild-type enzyme, pH 7.5, 25°C

650823

4.1.2.14

0.019

-

wild type enzyme, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

0.021

-

KA3-L1 variant, pH 7.5, 25°C

650823

4.1.2.14

0.04

-

mutant enzyme S184A, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

0.08

-

mutant enzyme S184L, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

0.1

-

KA1-1 variant, pH 7.5, 25°C

650823

4.1.2.14

0.11

-

KA1-4 variant, pH 7.5, 25°C

650823

4.1.2.14

0.11

-

mutant enzyme S184D, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

0.13

-

KA1-3 variant, pH 7.5, 25°C

650823

4.1.2.14

0.16

-

KA1-2 variant, pH 7.5, 25°C

650823

4.1.2.14

0.43

-

KA3-L2 variant, pH 7.5, 25°C

650823

4.1.2.14

0.58

-

KA2 variant, pH 7.5, 25°C

650823

4.1.2.14

1.09

-

KA3 variant, pH 7.5, 25°C

650823

4.1.2.14

6.08

-

KA2 variant, pH 7.5, 25°C

650823

4.1.2.14

6.08

-

KA3 variant, pH 7.5, 25°C

650823

2.7.1.178

2 entries

2.7.1.45

3 entries

4.1.2.14

15 entries

4.1.2.20

26.7

-

at 60°C in 50 mM sodium phosphate buffer (pH 6.2)

704334

4.1.2.51

24.2

-

pH 6.2, 60°C, recombinant enzyme

704334

4.1.2.51

26.7

-

pH 6.2, 60°C, enzyme purified from Picrophilus torridus

704334

4.1.2.55

28.2

-

60°C, pH not specified in the publication

719488

4.1.2.55

28.2

-

pH 6.0, 60°C

656156

4.1.2.55

28.2

-

pH 6.5, 70°C

722059

4.1.2.51

2 entries

4.1.2.55

3 entries

K_M Value (31 results)

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Show KM Value (31 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

13

-

at pH 7.9 and 25°C

745695

1.1.1.127

7.7

-

-

285820

2.7.1.11

8.8

-

at pH 8.0 and 42°C

738267

2.7.1.13

1.4

-

pH 8.0, temperature not specified in the publication

759808

2.7.1.178

0.14

-

pH 7.2, 60°C

672669

2.7.1.178

3.6

-

pH 7.5, 60°C

719488

2.7.1.45

0.027

-

in 50 mM Tris/HCl (pH 8.5) at 50°C

676988

2.7.1.45

0.027

-

pH 8.5, 50°C

676988

2.7.1.45

0.178

-

pH 7.0, 70°C, recombinant enzyme

657872

2.7.1.45

0.32

-

pH 7.4, 35°C, in presence of 5 mM MgCl2 and 0.1 M KCl

659714

2.7.1.45

1

-

-

636960, 636961

2.7.1.178

2 entries

2.7.1.45

5 entries

2.7.1.58

8.8

-

pH and temperature not specified in the publication

759203

4.1.2.14

1.5

-

mutant enzyme S184L, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

1.8

-

mutant enzyme S184D, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

1.9

-

wild type enzyme, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

2

-

KA3-L1 variant, pH 7.5, 25°C

650823

4.1.2.14

2.3

-

mutant enzyme S184A, in 100 mM HEPES, pH 7.5

682736

4.1.2.14

12

-

KA3-L2 variant, pH 7.5, 25°C

650823

4.1.2.14

13

-

KA3 variant, pH 7.5, 25°C

650823

4.1.2.14

14

-

KA2 variant, pH 7.5, 25°C

650823

4.1.2.14

25

-

KA1-2 variant, pH 7.5, 25°C

650823

4.1.2.14

49

-

KA1-3 variant, pH 7.5, 25°C

650823

4.1.2.14

55

-

KA1-4 variant, pH 7.5, 25°C

650823

4.1.2.14

65

-

KA1-1 variant, pH 7.5, 25°C

650823

4.1.2.14

285

-

wild-type enzyme, pH 7.5, 25°C

650823

4.1.2.14

13 entries

4.1.2.20

0.3

-

at 60°C in 50 mM sodium phosphate buffer (pH 6.2)

704334

4.1.2.51

0.3

-

pH 6.2, 60°C, enzyme purified from Picrophilus torridus

704334

4.1.2.51

0.4

-

pH 6.2, 60°C, recombinant enzyme

704334

4.1.2.55

25.7

-

60°C, pH not specified in the publication

719488

4.1.2.55

25.7

-

pH 6.0, 60°C

656156

4.1.2.55

25.7

-

pH 6.5, 70°C

722059

4.1.2.51

2 entries

4.1.2.55

3 entries

References & Links

Literature References (41)

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Show Reference (41 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4971

-

2-Keto-3-deoxy-6-phosphogluconic and related aldolases

1972

Wood, W.A.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

7

281-302

5899

4581499

Purification et proprietes de la D-mannonate hydrolase d'Escherichia coli'

1973

Robert-Baudouy, J.M.; Stoeber, F.R.

Biochim. Biophys. Acta

309

473-485

5900

6759855

D-Mannonate and D-altronate dehydratases of Escherichia coli K12

1982

Robert-Baudouy, J.; Jimeno-Abendano, J.; Stoeber, F.

Methods Enzymol.

90

288-294

5901

3038546

The role of iron in the activation of mannonic and altronic acid hydratases, two Fe-requiring hydro-lyases

1987

Dreyer, J.L.

Eur. J. Biochem.

166

623-630

5902

4388117

Aldohexuronic acid catabolism by a soil Aeromonas

1969

Farmer, J.J.; Eagon, R.G.

J. Bacteriol.

97

97-106

5903

13584413

A new pathway of uronic acid metabolism

1958

Ashwell, G.; Wahba, A.J.; Hickman, J.

Biochim. Biophys. Acta

30

186-187

285819

14488585

Alginic acid metabolism in bacteria. II. The enzymatic reduction of 4-deoxy-L-erythro-5-hexoseulose uronic acid to 2-keto-3-deoxy-D-gluconic acid

1962

Preiss, J.; Ashwell, G.

J. Biol. Chem.

237

317-321

285820

-

An enzyme in the pectinolytic pathway of Erwinia chrysanthemi: 2-Keto-3-deoxygluconate oxidoreductase

1984

Condemine, G.; Hugouvieux-Cotte-Pattat, N.; Robert-Baudouy, J.

J. Gen. Microbiol.

130

2839-2844

285821

13986017

Polygalacturonic acid metabolism in bacteria. II. Formation and metabolism of 3-deoxy-D-glycero-2,5-hexodiulosonic acid

1963

Preiss, J.; Ashwell, G.

J. Biol. Chem.

238

1577-1583

288145

4391087

Metabolism of the ketoaldehyde 2-keto-3-deoxyglucose

1968

Jellum, E.

Biochim. Biophys. Acta

165

357-363

288147

7763257

The presence of 2-keto-3-deoxygluconic acid and oxoaldehyde dehydrogenase activity in human erythrocytes

1995

Fujii, E.; Iwase, H.; Ishii-Karakasa, I.; Yajima, Y.; Hotta, K.

Biochem. Biophys. Res. Commun.

210

852-857

636960

13813474

Uronic acid metabolism in bacteria: IV. Purification and properties of 2-keto-3-deoxy-D-gluconokinase in Escherichia coli

1969

Cynkin, M.A.; Ashwell, G.

J. Biol. Chem.

235

1576-1579

636961

4944816

Study of the common degradative pathway of hexuronates in Escherichia coli K 12. Purification, properties and individuality of 2-keto-3-deoxy-D-gluconokinase

1971

Pouyssegur, J.; Stoeber, F.

Biochimie

53

771-781

644481

-

D-Glucosaminate

1984

Iwamoto, R.; Imanaga, Y.

Methods Enzym. Anal. , 3rd Ed. (Bergmeyer, H. U. , ed. )

5

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Links to other databases for 2-dehydro-3-deoxy-D-gluconate

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