Functional characterization of an NADPH dependent 2-alkyl-3-ketoalkanoic acid reductase involved in olefin biosynthesis in Stenotrophomonas maltophilia

Bonnett, S.A.; Papireddy, K.; Higgins, S.; del Cardayre, S.; Reynolds, K.A.; Biochemistry 50, 9633-9640 (2011)

Data extracted from this reference:

KM Value [mM]

KM Value Maximum [mM]

Substrate

Commentary

Organism

Structure

0.024

-

NADP+

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.026

-

NADPH

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.031

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.161

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.181

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.202

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.214

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

Natural Substrates

Organism

Commentary (Nat. Sub.)

Natural Products

Commentary (Nat. Pro.)

Organism (Nat. Pro.)

Reversibility

ID

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

Stenotrophomonas maltophilia

-

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

r

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

Stenotrophomonas maltophilia K279a

-

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

Stenotrophomonas maltophilia

-

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

Stenotrophomonas maltophilia K279a

-

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

r

Substrates

Commentary Substrates

Literature (Substrates)

Organism

Products

Commentary (Products)

Literature (Products)

Organism (Products)

Reversibility

Substrate Product ID

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

741882

Stenotrophomonas maltophilia

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

-

r

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

741882

Stenotrophomonas maltophilia K279a

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

-

r

(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

-

741882

Stenotrophomonas maltophilia

?

-

-

-

?

(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

-

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+

13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+

13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

741882

Stenotrophomonas maltophilia

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

741882

Stenotrophomonas maltophilia K279a

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

-

r

additional information

no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

additional information

no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

syn-2-decyl-3-hydroxytetradecanoic acid + NADPH + H+

100% activity

741882

Stenotrophomonas maltophilia

?

-

-

-

?

syn-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

15% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

syn-2-octyl-3-hydroxydodecanoic acid + NADPH + H+

20% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

Turnover Number Minimum [1/s]

Turnover Number Maximum [1/s]

Substrate

Commentary

Organism

Structure

0.97

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.2

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.3

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.4

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

2

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

Cofactor

Commentary

Organism

Structure

NADP+

-

Stenotrophomonas maltophilia

NADPH

-

Stenotrophomonas maltophilia

Cofactor

Commentary

Organism

Structure

NADP+

-

Stenotrophomonas maltophilia

NADPH

-

Stenotrophomonas maltophilia

KM Value [mM]

KM Value Maximum [mM]

Substrate

Commentary

Organism

Structure

0.024

-

NADP+

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.026

-

NADPH

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.031

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.161

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.181

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.202

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

0.214

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

Natural Substrates

Organism

Commentary (Nat. Sub.)

Natural Products

Commentary (Nat. Pro.)

Organism (Nat. Pro.)

Reversibility

ID

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

Stenotrophomonas maltophilia

-

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

r

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

Stenotrophomonas maltophilia K279a

-

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

Stenotrophomonas maltophilia

-

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

Stenotrophomonas maltophilia K279a

-

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

r

Substrates

Commentary Substrates

Literature (Substrates)

Organism

Products

Commentary (Products)

Literature (Products)

Organism (Products)

Reversibility

ID

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

741882

Stenotrophomonas maltophilia

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

-

r

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

741882

Stenotrophomonas maltophilia K279a

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

-

-

r

(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

-

741882

Stenotrophomonas maltophilia

?

-

-

-

?

(2R,3S)-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

-

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+

13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

(2R/2S)-2-hexyl-3-oxodecanoic acid + NADPH + H+

13% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

741882

Stenotrophomonas maltophilia

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

-

r

(R)-2-alkyl-3-oxoalkanoate + NADPH + H+

-

741882

Stenotrophomonas maltophilia K279a

(2R,3S)-2-alkyl-3-hydroxyalkanoate + NADP+

-

-

-

r

additional information

no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

additional information

no activity with syn-2-butyl-3-hydroxyoctanoic acid, 3-oxodecanoic acid, and 3-hydroxydecanoic acid

741882

Stenotrophomonas maltophilia K279a

?

-

-

-

?

syn-2-decyl-3-hydroxytetradecanoic acid + NADPH + H+

100% activity

741882

Stenotrophomonas maltophilia

?

-

-

-

?

syn-2-hexyl-3-hydroxydecanoic acid + NADPH + H+

15% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

syn-2-octyl-3-hydroxydodecanoic acid + NADPH + H+

20% activity compared to syn-2-decyl-3-hydroxytetradecanoic acid

741882

Stenotrophomonas maltophilia

?

-

-

-

?

Turnover Number Minimum [1/s]

Turnover Number Maximum [1/s]

Substrate

Commentary

Organism

Structure

0.97

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.2

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.3

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

1.4

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

2

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

kcat/KM Value [1/mMs^-1]

kcat/KM Value Maximum [1/mMs^-1]

Substrate

Commentary

Organism

Structure

6

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

6

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

7.3

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

9.6

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

47.9

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

KCat/KM Value [1/mMs^-1]

KCat/KM Value Maximum [1/mMs^-1]

Substrate

Commentary

Organism

Structure

6

-

(2R/2S)-2-hexyl-3-oxodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

6

-

syn-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

7.3

-

(2R,3S)-2-hexyl-3-hydroxydecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

9.6

-

syn-2-octyl-3-hydroxydodecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

47.9

-

syn-2-decyl-3-hydroxytetradecanoic acid

at pH 8.0 and 25°C

Stenotrophomonas maltophilia

No.

1st author

Pub Med

title

organims

journal

volume

pages

year

Activating Compound

Application

Cloned(Commentary)

Crystallization (Commentary)

Engineering

General Stability

Inhibitors

KM Value [mM]

Localization

Metals/Ions

Molecular Weight [Da]

Natural Substrates/ Products (Substrates)

Organic Solvent Stability

Organism

Oxidation Stability

Posttranslational Modification

Purification (Commentary)

Reaction

Renatured (Commentary)

Source Tissue

Specific Activity [micromol/min/mg]

Storage Stability

Substrates and Products (Substrate)

Subunits

Synonyms

Temperature Optimum [°C]

Temperature Range [°C]

Temperature Stability [°C]

Turnover Number [1/s]

pH Optimum

pH Range

pH Stability

Cofactor

Ki Value [mM]

pI Value

IC50 Value

Activating Compound (protein specific)

Application (protein specific)

Cloned(Commentary) (protein specific)

Cofactor (protein specific)

Crystallization (Commentary) (protein specific)

Engineering (protein specific)

General Stability (protein specific)

IC50 Value (protein specific)

Inhibitors (protein specific)

Ki Value [mM] (protein specific)

KM Value [mM] (protein specific)

Localization (protein specific)

Metals/Ions (protein specific)

Molecular Weight [Da] (protein specific)

Natural Substrates/ Products (Substrates) (protein specific)

Organic Solvent Stability (protein specific)

Oxidation Stability (protein specific)

Posttranslational Modification (protein specific)

Purification (Commentary) (protein specific)

Renatured (Commentary) (protein specific)

Source Tissue (protein specific)

Specific Activity [micromol/min/mg] (protein specific)

Storage Stability (protein specific)

Substrates and Products (Substrate) (protein specific)

Subunits (protein specific)

Temperature Optimum [°C] (protein specific)

Temperature Range [°C] (protein specific)

Temperature Stability [°C] (protein specific)

Turnover Number [1/s] (protein specific)

pH Optimum (protein specific)

pH Range (protein specific)

pH Stability (protein specific)

pI Value (protein specific)

Expression

General Information

General Information (protein specific)

Expression (protein specific)

KCat/KM [mM/s]

KCat/KM [mM/s] (protein specific)

742283

Kancharla

Stenotrophomonas maltophilia ...

Stenotrophomonas maltophilia, Stenotrophomonas maltophilia K279a

ChemBioChem

17

1426-1429

2016

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2

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-

2

-

1

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1

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1

-

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741882

Bonnett

Functional characterization o ...

Stenotrophomonas maltophilia, Stenotrophomonas maltophilia K279a

Biochemistry

50

9633-9640

2011

-

-

1

-

-

-

-

7

-

-

1

4

-

6

-

-

1

-

-

-

-

-

13

2

2

-

-

-

5

-

-

-

2

-

-

-

-

-

1

2

-

-

-

-

-

-

7

-

-

1

4

-

-

-

1

-

-

-

-

13

2

-

-

-

5

-

-

-

-

-

1

1

-

5

5