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Ligand D-Lactaldehyde

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.78

methylglyoxal + NADH = (R)-lactaldehyde + NAD+

207976, 207968, 207975, 137611, 207969

-

4.1.2.53

2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde

-

-

Substrate in Enzyme-catalyzed Reactions (11 results)

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Show Substrate (11 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.149

D-lactaldehyde + NADPH + H+ = ?

285999

-

1.1.1.2

D-lactaldehyde + NADPH + H+ = propane-1,2-diol + NADP+

286165, 286164, 286168

-

1.1.1.21

D-lactaldehyde + NADPH + H+ = ?

695881

-

1.1.1.21

D-lactoaldehyde + NADPH + H+ = ?

697266

-

1.2.1.22

(R)-lactaldehyde + NAD+ + H2O = (R)-lactate + NADH + 2 H+

697876

-

1.2.1.22

D-lactaldehyde + NAD+ + H2O = D-lactate + NADH + H+

288132, 288136, 674270

-

1.1.1.21

2 entries

1.2.1.22

2 entries

1.3.1.20

D-lactaldehyde + NADP+ = ?

349254

-

2.2.1.1

D-lactaldehyde + hydroxypyruvate = 5-deoxy-D-ribulose + ?

735416

-

4.1.2.14

pyruvate + D-lactaldehyde = ?

650823

-

4.1.2.17

Glycerone phosphate + (R)-lactaldehyde = 6-Deoxy-D-psicose 1-phosphate

5047, 5048, 5049

-

4.1.2.19

Glycerone phosphate + D-lactaldehyde = 6-Deoxy-D-sorbose 1-phosphate

5049, 5066

-

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.77

(R)-propane-1,2-diol + NAD+ = (R)-lactaldehyde + NADH

-

-

1.1.1.78

methylglyoxal + NADH = (R)-lactaldehyde + NAD+

207976, 207968, 207975, 137611, 207969

-

4.1.2.18

2-Keto-3-deoxy-D-fuconate = Pyruvate + D-lactaldehyde

5058,

-

4.1.2.19

6-Deoxy-L-sorbose 1-phosphate = Glycerone phosphate + D-lactaldehyde

-

-

4.1.2.53

2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde

-

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.2.1.2

-

719298

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.2

13.7

-

-

286165

1.1.1.21

0.283

-

in 0.1 M potassium phosphate, pH 7.4

697266

1.1.1.21

1.87

-

in 0.1 M potassium phosphate, pH 7.4, at 25°C

695881

1.1.1.21

2 entries

1.2.1.22

2

-

100 mM TES pH 7.5, 2.5 mM NAD+

674270

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

1.1.1.149

0.534

0.587

-

285999

1.1.1.149

0.587

-

-

285999

1.1.1.21

0.073

-

in 0.1 M potassium phosphate, pH 7.4

697266

1.1.1.21

0.74

-

in 0.1 M potassium phosphate, pH 7.4, at 25°C

695881

1.2.1.22

0.302

-

100 mM TES pH 7.5, 2.5 mM NAD+

674270

1.2.1.22

5.6

-

-

288136

1.1.1.149

2 entries

1.1.1.21

2 entries

1.2.1.22

2 entries

2.2.1.1

8.4

-

at pH 7.2 and 50°C

735416

References & Links

Literature References (24)

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Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

5047

13898172

The metabolism of L-fucose. II. The enzymatic cleavage of L-fuculose 1-phosphate

1962

Ghalambor, M.A.; Heath, E.C.

J. Biol. Chem.

237

2427-2433

5048

-

L-Fuculose 1-phosphate aldolase

1966

Ghalambor, M.A.; Heath, E.C.

Methods Enzymol.

9

538-542

5049

-

Other deoxy sugar aldolases

1972

Feingold, D.S.; Hoffee, P.A.

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

7

303-321

5058

5016652

D-Fucose metabolism in a pseudomonad. IV. Cleavage of 2-keto-3-deoxy-D-fuconate to pyruvate and D-lactaldehyde by 2-keto-3-deoxy-L-arabonate aldolase

1972

Dahms, A.S.; Anderson, R.L.

J. Biol. Chem.

247

2238-2241

5066

4975916

L-Rhamnulose 1-phosphate aldolase from Escherichia coli. Crystallization and properties

1969

Chiu, T.H.; Feingold, D.S.

Biochemistry

8

98-108

137611

-

Formation of D(-)-1,2-propanediol and D(-)-lactate from glucose by Clostridium sphenoides under phosphate limitation

1985

Tran-Din, K.; Gottschalk, G.

Arch. Microbiol.

142

87-92

207968

14323585

The metabolism of lactaldehyde: VII. The oxidation of D-lactaldehyde in rat liver

1965

Ting, S.M.; Miller, O.N.; Sellinger, O.Z.

Biochim. Biophys. Acta

97

407-415

207969

6386056

Purification and partial characterization of a methylglyoxal reductase from goat liver

1984

Ray, M.; Ray, S.

Biochim. Biophys. Acta

802

119-127

207975

-

Purification and partial characterization of NADH-dependent methylglyoxal-reducing enzyme from porcine liver

1988

Kato, H.; Miyauchi, Y.; Nishimura, T.; Liang, Z.Q.

Agric. Biol. Chem.

52

2641-2642

207976

-

Metabolism of 2-oxoaldehydes in bacteria: purification and characterization of methylglyoxal reductase from Escherichia coli

1987

Saikusa, T.; Rhee, H.; Watanabe, K.; Murata, K.; Kimura, A.

Agric. Biol. Chem.

51

1893-1899

285999

7484385

Substrate specificity and kinetic mechanism of Tetrahymena 20alpha-hydroxysteroid dehydrogenase

1995

Hara, A.; Inazu, A.; Deyashiki, Y.; Nozawa, Y.

Adv. Exp. Med. Biol.

372

249-258

286164

4393513

Purification and characterization of a reduced nicotinamide adenine dinucleotide phosphate-linked aldehyde reductase from brain

1970

Tabakoff, B.; Erwin, G.

J. Biol. Chem.

245

3263-3268

286165

4402936

Triphosphopyridine nucleotide-linked aldehyde reductase I. Purification and properties of the enzyme from pig kidney cortex

1972

Bosron, W.F.; Prairie, R.L.

J. Biol. Chem.

217

4480-4485

286168

16919

Purification and properties of NADPH-dependent aldehyde reductase from human liver

1977

Wermuth, B.; Muench, J.D.B.; von Wartburg, J.P.

J. Biol. Chem.

252

3821-3828

288132

3908097

Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae

1985

Inoue, Y.; Watanabe, K.; Shimosaka, M.; Saikusa, T.; Fukuda, Y.; Murata, K.; Kimura, A.

Eur. J. Biochem.

153

243-247

288136

4319789

Threonine metabolism in a strain of Bacillus subtilis: enzymic oxidation of the intermediate DL-lactaldehyde

1970

Willetts, A.J.; Turner, J.M.

Biochim. Biophys. Acta

222

234-236

349254

7852295

Purification and characterization of dimeric dihydrodiol dehydrogenase from dog liver

1994

Sato, K.; Nakanishi, M.; Deyashiki, Y.; Hara, A.; Matsuura, K.; Ohya, I.

J. Biochem.

116

711-717

650823

11094340

Directed evolution of D-2-keto-3-deoxy-6-phosphogluconate aldolase to new variants for the efficient synthesis of D- and L-sugars

2000

Fong, S.; Machajewski, T.D.; Mak, C.C.; Wong, C.

Chem. Biol.

7

873-883

674270

16585745

Identification of lactaldehyde dehydrogenase in Methanocaldococcus jannaschii and its involvement in production of lactate for F420 biosynthesis

2006

Grochowski, L.L.; Xu, H.; White, R.H.

J. Bacteriol.

188

2836-2844

695881

19464995

Kinetic studies of AKR1B10, human aldose reductase-like protein: endogenous substrates and inhibition by steroids

2009

Endo, S.; Matsunaga, T.; Mamiya, H.; Ohta, C.; Soda, M.; Kitade, Y.; Tajima, K.; Zhao, H.T.; El-Kabbani, O.; Hara, A.

Arch. Biochem. Biophys.

487

1-9

697266

18845131

Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress

2009

Endo, S.; Matsunaga, T.; Mamiya, H.; Hara, A.; Kitade, Y.; Tajima, K.; El-Kabbani, O.

Chem. Biol. Interact.

178

151-157

697876

18793327

Metabolic fate of L-lactaldehyde derived from an alternative L-rhamnose pathway

2008

Watanabe, S.; Piyanart, S.; Makino, K.

FEBS J.

275

5139-5149

719298

21290439

Broadening deoxysugar glycodiversity: natural and engineered transaldolases unlock a complementary substrate space

2011

Rale, M.; Schneider, S.; Sprenger, G.A.; Samland, A.K.; Fessner, W.D.

Chemistry

17

2623-2632

735416

-

Engineering a thermostable transketolase for unnatural conversion of (2S)-hydroxyaldehydes

2015

Abdoul Zabar, J.; Lorilliere, M.; Yi, D.; Thangavelu, S.; Devamani, T.; Nauton, L.; Charmantray, F.; Helaine, V.; Fessner, W.; Hecquet, L.

Adv. Synth. Catal.

357

1715-1720

Links to other databases for D-Lactaldehyde

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Show Links (1 entry)

ChEBI

PubChem

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