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Ligand (2S)-ethylmalonyl-CoA

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for (2S)-ethylmalonyl-CoA

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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

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.3.1.85

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(E)-crotonyl-CoA + CO2 + NADPH + H+ = (2S)-ethylmalonyl-CoA + NADP+

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1.3.1.85

-

crotonyl-CoA + CO2 + NADPH + H+ = (2S)-ethylmalonyl-CoA + NADP+

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1.3.1.85

2 entries

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

2.3.1.94

736307

propanoyl-CoA + 5 (2S)-methylmalonyl-CoA + (2S)-ethylmalonyl-CoA + 6 NADPH + 6 H+ = (3R,4S,5R,6R)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydro-2H-pyran-2-one + ?

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2.3.1.94

736307

propanoyl-CoA + 5 (2S)-methylmalonyl-CoA + (2S)-ethylmalonyl-CoA + 6 NADPH + 6 H+ = (3R,5R,6S)-6-[(2S,3R)-3-hydroxypentan-2-yl]-3,5-dimethyldihydro-2H-pyran-2,4(3H)-dione + ?

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2.3.1.94

736307

propanoyl-CoA + 5 (2S)-methylmalonyl-CoA + (2S)-ethylmalonyl-CoA + 6 NADPH + 6 H+ = 8-ethyl-8-desmethyl-6-deoxyerythronolide B + 7 CoA + 6 CO2 + H2O + 6 NADP+

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2.3.1.94

3 entries

4.1.1.94

717859

(S)-ethylmalonyl-CoA = butanoyl-CoA + CO2

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5.1.99.1

747542, 693174

(2S)-ethylmalonyl-CoA = (2R)-ethylmalonyl-CoA

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Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.1.85

-

(E)-crotonyl-CoA + CO2 + NADPH + H+ = (2S)-ethylmalonyl-CoA + NADP+

-

1.3.1.85

-

crotonyl-CoA + CO2 + NADPH + H+ = (2S)-ethylmalonyl-CoA + NADP+

-

1.3.1.85

-

crotonyl-CoA + NADPH + CO2 + H+ = (2S)-ethylmalonyl-CoA + NADP+

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1.3.1.85

3 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

COMMENTARY

EC NUMBER

LITERATURE

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

in 100 mM Tris-HCl buffer (pH 7.9), temperature not specified in the publication

1.3.1.85

689745

104

-

pH 7.1, 30°C, recombinant enzyme in absence of ATP-Mg2-

4.1.1.94

717859

9.5

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pH 7.1, 30°C, recombinant enzyme in presence of 5 mM ATP-Mg2-

4.1.1.94

717859

10

-

K_M Value (4 results)

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Show KM Value (4 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

in 100 mM Tris-HCl buffer (pH 7.9), temperature not specified in the publication

1.3.1.85

0.2

-

689745

pH 7.1, 30°C, recombinant enzyme in absence of ATP-Mg2-

4.1.1.94

0.00096

-

717859

pH 7.1, 30°C, recombinant enzyme in presence of 5 mM ATP-Mg2-

4.1.1.94

0.0065

-

717859

-

5.1.99.1

0.04

-

693174

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

689745

17548827

Synthesis of C5-dicarboxylic acids from C2-units involving crotonyl-CoA carboxylase/reductase: the ethylmalonyl-CoA pathway

2007

Erb, T.J.; Berg, I.A.; Brecht, V.; Mueller, M.; Fuchs, G.; Alber, B.E.

Proc. Natl. Acad. Sci. USA

104

10631-10636

693174

18819910

Ethylmalonyl-CoA mutase from Rhodobacter sphaeroides defines a new subclade of coenzyme B12-dependent acyl-CoA mutases

2008

Erb, T.J.; Retey, J.; Fuchs, G.; Alber, B.E.

J. Biol. Chem.

283

32283-32293

717859

22016388

Ethylmalonyl-CoA decarboxylase, a new enzyme involved in metabolite proofreading

2011

Linster, C.L.; Noel, G.; Stroobant, V.; Vertommen, D.; Vincent, M.F.; Bommer, G.T.; Veiga-da-Cunha, M.; Van Schaftingen, E.

J. Biol. Chem.

286

42992-43003

736307

24161212

In vitro reconstitution and analysis of the 6-deoxyerythronolide B synthase

2013

Lowry, B.; Robbins, T.; Weng, C.H.; OBrien, R.V.; Cane, D.E.; Khosla, C.

J. Am. Chem. Soc.

135

16809-16812

747542

26716911

Use of methylmalonyl-CoA epimerase in enhancing crotonase stereoselectivity

2016

Hamed, R.B.; Gomez-Castellanos, J.R.; Sean Froese, D.; Krysztofinska, E.; Yue, W.W.; Schofield, C.J.

ChemBioChem

17

471-473

Links to other databases for (2S)-ethylmalonyl-CoA

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Show Links (1 entry)

ChEBI

PubChem

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