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Ligand (3S,5S)-carbapenam 3-carboxylate

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for (3S,5S)-carbapenam 3-carboxylate

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.14.20.3

722055

(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

4oj8, 3D-view

1.14.20.3

722442

(3S,5S)-carbapen-2-am-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

4oj8, 3D-view

1.14.20.3

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

6.3.3.6

-

ATP + (2S,5S)-5-carboxymethylproline = AMP + diphosphate + (3S,5S)-carbapenam 3-carboxylate

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Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.14.20.3

722055, 722443, 722441, 743903

(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

4oj8, 3D-view

1.14.20.3

722442

(3S,5S)-carbapen-2-am-3-carboxylate + 2-oxoglutarate + O2 = (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

4oj8, 3D-view

1.14.20.3

2 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

6.3.3.6

-

ATP + (2S,5S)-5-carboxymethylproline = AMP + diphosphate + (3S,5S)-carbapenam 3-carboxylate

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Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

-

6.3.3.6

721590

-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.20.3

4oj8, 3D-view

Enzyme Kinetic Parameters

K_i Value (3 results)

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Show KI Value (3 entries)

COMMENTARY

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

LITERATURE

pH 7.8, 22°C, variable substrate: (2S,5R)-carboxymethylproline, Ki(intercept)

6.3.3.6

1.1

-

721590

pH 7.8, 22°C, variable substrate: (2S,5R)-carboxymethylproline, Ki(slope)

6.3.3.6

1.3

-

721590

pH 7.8, 22°C, variable substrate: ATP, Ki(slope)

6.3.3.6

1.3

-

721590

References & Links

Literature References (6)

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Show Reference (6 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

721590

12820893

Inhibition and alternate substrate studies on the mechanism of carbapenam synthetase from Erwinia carotovora

2003

Gerratana, B.; Stapon, A.; Townsend, C.A.

Biochemistry

42

7836-7847

722055

15174175

Biosynthesis of carbapenem antibiotics: new carbapenam substrates for carbapenem synthase (CarC)

2004

Sleeman, M.C.; Smith, P.; Kellam, B.; Chhabra, S.R.; Bycroft, B.W.; Schofield, C.J.

Chembiochem

5

879-882

722441

14677956

Synthesis of (3S,5R)-carbapenam-3-carboxylic acid and its role in carbapenem biosynthesis and the stereoinversion problem

2003

Stapon, A.; Li, R.; Townsend, C.A.

J. Am. Chem. Soc.

125

15746-15747

722442

12848554

Carbapenem biosynthesis: confirmation of stereochemical assignments and the role of CarC in the ring stereoinversion process from L-proline

2003

Stapon, A.; Li, R.; Townsend, C.A.

J. Am. Chem. Soc.

125

8486-8493

722443

15303862

The unusual bifunctional catalysis of epimerization and desaturation by carbapenem synthase

2004

Topf, M.; Sandala, G.M.; Smith, D.M.; Schofield, C.J.; Easton, C.J.; Radom, L.

J. Am. Chem. Soc.

126

9932-9933

743903

-

Uncoupled epimerization and desaturation by carbapenem synthase mechanistic insights from QM/MM studies

2015

Ma, G.; Zhu, W.; Su, H.; Cheng, N.; Liu, Y.

ACS Catal.

5

5556-5566

Links to other databases for (3S,5S)-carbapenam 3-carboxylate

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Show Links (1 entry)

ChEBI

PubChem

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