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Enzyme Kinetic Parameters
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Ligand 2,3,4,5-tetrahydrodipicolinic acid

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Basic Ligand Information

Molecular Structure

Picture of 2,3,4,5-tetrahydrodipicolinic acid (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₇H₉NO₄

2,3,4,5-tetrahydrodipicolinic acid

CXMBCXQHOXUCEO-UHFFFAOYSA-N

Synonyms:

2,3,4,5-tetrahydrodipicolinate, 2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid, delta-piperidine-2,6-dicarboxylate, DELTA1-piperidine-2,6-dicarboxylate, tetrahydrodipicolinate, tetrahydrodipicolinic acid

Pathway Source

Pathways

KEGG

Biosynthesis of amino acids, Biosynthesis of secondary metabolites, Lysine biosynthesis, Microbial metabolism in diverse environments, Monobactam biosynthesis

MetaCyc

L-lysine biosynthesis I, L-lysine biosynthesis II, L-lysine biosynthesis III, L-lysine biosynthesis VI, tabtoxinine-beta-lactam biosynthesis

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Roles as Enzyme Ligand

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

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.6.1.83

L-glutamate + tetrahydrodipicolinate + H2O = LL-diaminopimelate + 2-oxoglutarate

725250

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.1.8

2,3-dihydrodipicolinate + NAD(P)H = 2,3,4,5-tetrahydrodipicolinate + NAD(P)+

0, 390620, 390621, 390623, 390624, 390625, 390619

1.17.1.8

dihydrodipicolinate + NADH + H+ = tetrahydrodipicolinate + NAD+

1.17.1.8

2 entries

2.6.1.83

LL-diaminopimelate + 2-oxoglutarate = L-glutamate + tetrahydrodipicolinate + H2O

Substrate in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.117

succinyl-CoA + tetrahydrodipicolinate = ?

486148, 486149, 686773

2.3.1.117

succinyl-CoA + tetrahydrodipicolinate = CoA + (2S)-2-(3-carboxypropanamido)-6-oxoheptanedioate

L-glutamate + tetrahydrodipicolinate + H2O = LL-diaminopimelate + 2-oxoglutarate

724426, 723845, 725250, 726273

Product in Enzyme-catalyzed Reactions (14 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.1.8

2,3-dihydrodipicolinate + 3'-NADPH + H+ = 2,3,4,5-tetrahydrodipicolinate + 3'-NADP+ + H2O

1.17.1.8

2,3-dihydrodipicolinate + alpha-NADPH + H+ = 2,3,4,5-tetrahydrodipicolinate + alpha-NADP+ + H2O

1.17.1.8

2,3-dihydrodipicolinate + NAD(P)H = 2,3,4,5-tetrahydrodipicolinate + NAD(P)+

0, 390619, 390620, 390624, 390623, 390621, 390625

1.17.1.8

2,3-dihydrodipicolinate + NADH + H+ = 2,3,4,5-tetrahydrodipicolinate + NAD+ + H2O

1.17.1.8

2,3-dihydrodipicolinate + reduced 3-acetylpyridine adenine dinucleotide = 2,3,4,5-tetrahydrodipicolinate + oxidized 3-acetylpyridine adenine dinucleotide

390624

1.17.1.8

2,3-dihydrodipicolinate + reduced 3-acetylpyridine adenine dinucleotide = 2,3,4,5-tetrahydrodipicolinate + oxidized 3-acetylpyridine adenine dinucleotide + H2O

1.17.1.8

2,3-dihydrodipicolinate + reduced nicotinamide hypoxanthine dinucleotide phosphate = 2,3,4,5-tetrahydrodipicolinate + oxidized nicotinamide hypoxanthine dinucleotide phosphate + H2O

1.17.1.8

2,3-dihydrodipicolinate + thio-NADPH + H+ = 2,3,4,5-tetrahydrodipicolinate + thio-NADP+ + H2O

1.17.1.8

dihydrodipicolinate + NADH + H+ = tetrahydrodipicolinate + NAD+

2.6.1.83

LL-2,6-diaminopimelate + 2-oxoglutarate = 2,3,4,5-tetrahydrodipicolinate + L-glutamate + H2O

2.6.1.83

LL-diaminopimelate + 2-oxoglutarate = L-glutamate + tetrahydrodipicolinate + H2O

2.6.1.83

meso-diaminopimelate + 2-oxoglutarate = L-glutamate + tetrahydrodipicolinate + H2O

5.1.1.7

DL-3-fluoro-2,6-diaminopimelic acid = tetrahydrodipicolinic acid + HF

651569

5.1.1.7

LL-3-fluoro-2,6-diaminopimelic acid = tetrahydrodipicolinic acid + HF

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.6.1.83

1.1

pH 7.6, 30°C

726273

K_M Value (4 results)

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Show KM Value (4 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

0.02

0.022

0.19

pH 7.5, 25°C

0.1

pH 7.6, 30°C

726273

References & Links

Literature References (15)

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Show Reference (15 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

390619

4378965

The reduction step in diaminopimelic acid biosynthesis

1965

Farkas, W.; Gilvarg, C.

J. Biol. Chem.

240

4717-4722

390620

Escherichia coli dihydrodipicolinate synthase and dihydrodipicolinate reductase: kinetic and inhibition studies of two putative herbicide targets

1999

Coulter, C.V.; Gerrard, J.A.; Kraunsoe, J.A.E.; Pratt, A.J.

Pestic. Sci.

887-895

390621

8873595

Interaction of pyridine nucleotide substrates with Escherichia coli dihydrodipicolinate reductase: Thermodynamic and structural analysis of binary complexes

1996

Reddy, S.G.; Scapin, G.; Blanchard, J.S.

Biochemistry

13294-13302

390623

11342032

Inhibitors of dihydrodipicolinate reductase, a key enzyme of the diaminopimelate pathway of Mycobacterium tuberculosis

2001

Paiva, A.M.; Vanderwall, D.E.; Blanchard, J.S.; Kozarich, J.W.; Williamson, J.M.; Kelly, T.M.

Biochim. Biophys. Acta

1545

67-77

390624

7893644

Expression, purification, and characterization of Escherichia coli dihydrodipicolinate reductase

1995

Reddy, S.G.; Sacchettini, J.C.; Blanchard, J.S.

Biochemistry

3492-3501

390625

9398235

Three-dimensional structure of Escherichia coli dihydrodipicolinate reductase in complex with NADH and the inhibitor 2,6-pyridinedicarboxylate

1997

Scapin, G.; Reddy, S.G.; Zheng, R.; Blanchard, J.S.

Biochemistry

15081-15088

486148

6365916

Purification and characterization of succinyl-CoA: tetrahydrodipicolinate N-succinyltransferase from Escherichia coli

1984

Simms, S.A.; Voige, W.H.; Gilvarg, C.

J. Biol. Chem.

259

2734-2741

486149

3700390

Studies on the active site of succinyl-CoA:tetrahydrodipicolinate N-succinyltransferase. Characterization using analogs of tetrahydrodipicolinate

1986

Berges, D.A.; DeWolf, W.E.; Dunn, G.L.; Newmann, D.J.; Schmidt, S.J.; Taggart, J.J.; Gilvarg, C.

J. Biol. Chem.

261

6160-6167

651569

Identification of active site cysteine residues that function as general bases: diaminopimelate epimerase

2000

Koo, C.W.; Sutherland, A.; Vederas, J.C.; Blanchard, J.S.

J. Am. Chem. Soc.

122

6122-6123

686773

18242192

Structure of Escherichia coli tetrahydrodipicolinate N-succinyltransferase reveals the role of a conserved C-terminal helix in cooperative substrate binding

2008

Nguyen, L.; Kozlov, G.; Gehring, K.

FEBS Lett.

582

623-626

723845

21206046

Crystallization and preliminary X-ray diffraction analysis of L,L-diaminopimelate aminotransferase (DapL) from Chlamydomonas reinhardtii

2011

Hudson, A.O.; Giron, I.; Dobson, R.C.

Acta Crystallogr. Sect. F

140-143

724426

21435399

Structural insights for the substrate recognition mechanism of LL-diaminopimelate aminotransferase

2011

Watanabe, N.; James, M.N.

Biochim. Biophys. Acta

1814

1528-1533

725250

20418392

Methanococci use the diaminopimelate aminotransferase (DapL) pathway for lysine biosynthesis

2010

Liu, Y.; White, R.H.; Whitman, W.B.

J. Bacteriol.

192

3304-3310

726273

21633707

L,L-diaminopimelate aminotransferase from Chlamydomonas reinhardtii: a target for algaecide development

2011

Dobson, R.C.; Giron, I.; Hudson, A.O.

PLoS ONE

e20439

755963

29307827

Functional chararacterization of the enzymes TabB and TabD involved in tabtoxin biosynthesis by Pseudomonas syringae

2018

Manning, M.E.; Danson, E.J.; Calderone, C.T.

Biochem. Biophys. Res. Commun.

496

212-217

Links to other databases for 2,3,4,5-tetrahydrodipicolinic acid

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PubChem

Ligand 2,3,4,5-tetrahydrodipicolinic acid

Basic Ligand Information

Roles as Enzyme Ligand

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

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (3 results)

Product in Enzyme-catalyzed Reactions (14 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

KM Value (4 results)

References & Links

Literature References (15)

Links to other databases for 2,3,4,5-tetrahydrodipicolinic acid

k_cat Value (Turnover Number) (1 result)

K_M Value (4 results)