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Ligand adenylosuccinate

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for adenylosuccinate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Natural Substrate (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

2ptr, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

2vd6, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

5nx9, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

2ptr, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

2vd6, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

5nx9, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

2ptr, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

2vd6, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

5nx9, 3D-view

4.3.2.2

9 entries

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.4

GTP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

0

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + adenylosuccinate

651921, 649423, 650258, 652965, 651925, 652500, 652193, 649897, 652347, 651884, 652812, 649264, 649265, 652608, 652317, 652356, 649670, 653751, 652929, 0

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP

652608

1mez, 3D-view

6.3.4.4

3 entries

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

2ptr, 3D-view

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

2vd6, 3D-view

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

5nx9, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

2ptr, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

2vd6, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

5nx9, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

2ptr, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

2vd6, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

5nx9, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

2ptr, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

2vd6, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

5nx9, 3D-view

4.3.2.2

12 entries

Product in Enzyme-catalyzed Reactions (13 results)

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Show Product (13 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

2ptr, 3D-view

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

2vd6, 3D-view

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

5nx9, 3D-view

6.3.4.4

2'-dGTP + IMP + L-aspartate = 2'-dGDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

ATP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

0

1mez, 3D-view

6.3.4.4

ddGTP + IMP + L-aspartate = ddGDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

GTP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

1537, 0, 1533, 1534, 1542, 1553, 1554, 1555, 1556, 1558, 1559, 1560, 1561, 1562, 1563, 1564, 1565, 1566, 1567, 1568, 1548, 1569, 1535, 1539, 1545, 1546, 1570, 1540, 1543, 1547, 1549, 1571, 1572, 1536, 1552, 1550, 1541, 1538, 1551, 1557, 1544

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + adenylosuccinate

649264, 651921, 652193, 652500, 649423, 649897, 651884, 652608, 649265, 649670, 650258, 652965, 653751, 0, 652929, 651925, 652347, 652356, 652812, 652317

1mez, 3D-view

6.3.4.4

ITP + IMP + L-Asp = IDP + phosphate + adenylosuccinate

1561, 0

1mez, 3D-view

6.3.4.4

ITP + IMP + L-aspartate = IDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

UTP + IMP + L-Asp = UDP + phosphate + adenylosuccinate

1561

1mez, 3D-view

6.3.4.4

XTP + IMP + L-Asp = XDP + phosphate + adenylosuccinate

1561

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP

0, 652608

1mez, 3D-view

4.3.2.2

3 entries

6.3.4.4

10 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.4

-

1537, 1546, 1549, 649670, 652500

1mez, 3D-view

6.3.4.4

competitive inhibitor of IMP, noncompetitive inhibitor of GTP and aspartate

726945

1mez, 3D-view

6.3.4.4

competitive versus IMP, non-competitive versus GTP and aspartate

662801

1mez, 3D-view

6.3.4.4

competitive with respect to IMP

1548

1mez, 3D-view

6.3.4.4

feedback inhibition

652317

1mez, 3D-view

6.3.4.4

5 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (19 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (19 entries)

EC NUMBER

ENZYME 3D STRUCTURE

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

18 entries

6.3.4.4

1mez, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (8 results)

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Show Turnover Number (8 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.3.2.2

0.00048

-

mutant T140A

682738

4.3.2.2

0.00689

-

mutant S306A

682738

4.3.2.2

0.01

-

mutant T93A

682738

4.3.2.2

0.1

-

pH 7.6, 37°C

729717

4.3.2.2

0.7

-

pH 7.6, 37°C

729717

4.3.2.2

1.14

-

mutant S94A

682738

4.3.2.2

1.74

-

wild-type enzyme

682738

4.3.2.2

7.5

-

pH 7.4, 25°C

691116

4.3.2.2

8 entries

K_M Value (42 results)

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Show KM Value (42 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.3.2.2

0.0012

-

-

34451

4.3.2.2

0.0013

-

mutant D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0014

-

recombinant His-tagged mutant R426H, pH 7.4, 25°C

729296

4.3.2.2

0.00146

-

histidine-tagged enzyme

682657

4.3.2.2

0.0015

-

mutant D69E

682733

4.3.2.2

0.0015

-

-

34449

4.3.2.2

0.00177

-

wild-type enzyme

682738

4.3.2.2

0.00178

-

none-tagged enzyme

682657

4.3.2.2

0.002

-

mutant D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0021

-

wild-type enzyme

682733

4.3.2.2

0.0021

-

recombinant His-tagged wild-type enzyme, pH 7.4, 25°C

729296

4.3.2.2

0.00224

-

mutant S94A

682738

4.3.2.2

0.00254

-

enzyme from cell line 1751

34462

4.3.2.2

0.0027

-

wild type, 50 mM HEPES, pH 7.0, 25°C

664041

4.3.2.2

0.0027

-

recombinant His-tagged mutant R303C, pH 7.4, 25°C

729296

4.3.2.2

0.00289

-

enzyme from cell line 1753

34462

4.3.2.2

0.0033

-

-

1541

4.3.2.2

0.0033

-

enzyme from wild-type cell lines

34462

4.3.2.2

0.004

-

50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0043

-

mutant I62E/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0046

-

mutant D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0047

-

-

34457

4.3.2.2

0.0061

-

mutant I62E/D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0071

-

mutant R310K

682733

4.3.2.2

0.0091

-

wild-type enzyme, pH 8.1, 37°C

730526

4.3.2.2

0.0093

-

mutant D69N

682733

4.3.2.2

0.0107

-

mutant I62D/D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.012

-

-

34458

4.3.2.2

0.0128

-

mutant S306A

682738

4.3.2.2

0.013

-

-

34456

4.3.2.2

0.0166

-

mutant Q212E, 50 mM HEPES, pH 7.0, 25°C

664041

4.3.2.2

0.0175

-

mutant I62E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0177

-

mutant T93A

682738

4.3.2.2

0.0177

-

mutant I62D/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0181

-

mutant I62E/D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0192

-

mutant T140A

682738

4.3.2.2

0.023

-

mutant R310Q

682733

4.3.2.2

0.032

-

pH 7.4, 25°C

691116

4.3.2.2

0.0437

-

pH 7.6, 37°C

729717

4.3.2.2

0.0488

-

mutant I62D/D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0551

-

mutant I62D, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.2042

-

pH 7.6, 37°C

729717

4.3.2.2

42 entries

K_i Value (7 results)

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Show KI Value (7 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

6.3.4.4

0.0094

-

pH 6.0, 70°C, competitive inhibition of IMP

726945

6.3.4.4

0.016

-

pH 6.7, 22°C, AdSS2

652500

6.3.4.4

0.021

-

pH 6.7, 22°C, AdSS1

652500

6.3.4.4

0.029

-

pH 7.5

662801

6.3.4.4

0.0426

-

pH 6.0, 70°C, noncompetitive inhibition of aspartate

726945

6.3.4.4

0.0429

-

pH 6.0, 70°C, noncompetitive inhibition of GTP

726945

6.3.4.4

2.7

-

pH 8.0, 25°C

649670

6.3.4.4

7 entries

References & Links

Literature References (97)

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Show Reference (97 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1533

3045328

Preliminary X-ray crystallographic study of adenylosuccinate synthetase from Escherichia coli

1988

Serra, M.A.; Bass, M.B.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

200

753-754

1534

3038024

Overproduction, purification, and characterization of adenylosuccinate synthetase from Escherichia coli

1987

Bass, M.B.; Fromm, H.J.; Stayton, M.M.

Arch. Biochem. Biophys.

256

335-342

1535

3542024

Isotope exchange at equilibrium studies with rat muscle adenylosauccinate synthetase

1986

Cooper, B.F.; Fromm, H.J.; Rudolph, F.B.

Biochemistry

25

7323-7327

1536

6703692

Adenylosuccinate synthetase from Dictyostelium discoideum: effects of hadacidin analogs and binding of [14C]hadacidin

1984

Jahngen, E.G.E.; Rossomando, E.F.

Arch. Biochem. Biophys.

229

145-154

1537

6347525

Regulation, genetics, and properties of adenylosuccinate synthetase

1983

Stayton, M.M.; Rudolph, F.B.; Fromm, H.J.

Curr. Top. Cell. Regul.

22

103-141

1538

6351751

Nitro analogs of substrates for adenylosuccinate synthetase and adenylosuccinate lyase

1983

Porter, D.J.T.; Rudie, N.G.; Bright, H.J.

Arch. Biochem. Biophys.

225

157-163

1539

7213642

Purification and properties of adenylosuccinate synthetase from Yoshida sarcoma ascites tumor cells

1980

Matsuda, Y.; Shimura, K.; Shiraki, H.; Nakagawa, H.

Biochim. Biophys. Acta

616

340-350

1540

529280

Preliminary crystallographic data for adenylosuccinate synthetase from rabbit skeletal muscle

1979

Harada, S.; Matsuura, Y.; Tanaka, N.; Kakudo, M.; Matsuda, Y.; Ogawa, H.; Shiraki, H.; Nakagawa, H.

J. Mol. Biol.

132

729-731

1541

468834

Specificity of adenylosuccinate synthetase and adenylosuccinate lyase from Leishmania donovani. Selective amination of an antiprotozoal agent

1979

Spector, T.; Jones, T.E.; Elion, G.B.

J. Biol. Chem.

254

8422-8426

1542

372184

Guanosine 5'-diphosphate-3'-diphosphate inhibition of adenylosuccinate synthetase

1979

Stayton, M.M.; Fromm, H.J.

J. Biol. Chem.

254

2579-2581

1543

692386

Adenylosuccinate synthetase (rabbit muscle, heart, and liver)

1978

Fischer, H.E.; Muirhead, K.M.; Bishop, S.H.

Methods Enzymol.

51

207-213

1544

21629

Adenylosuccinate synthetase from Azotobacter vinelandii: purification, properties and steady-state kinetics

1977

Markham, G.D.; Reed, G.H.

Arch. Biochem. Biophys.

184

24-35

1545

71897

Adenylosuccinate synthetase in rat liver: the existence of two types and their regulatory roles

1977

Matsuda, Y.; Ogawa, H.; Fukutome, S.; Shiraki, H.; Nakagawa, H.

Biochem. Biophys. Res. Commun.

78

766-771

1546

18452

Purification, crystallization, and properties of adenylosuccinate synthetase from rat skeletal muscle

1977

Ogawa, H.; Shiraki, H.; Matsuda, Y.; Kakiuchi, K.; Nakagawa, H.

J. Biochem.

81

859-869

1547

953040

Mammalian adenylosuccinate synthetase. Nucleotide monophosphate substrates and inhibitors

1976

Spector, T.; Miller, R.L.

Biochim. Biophys. Acta

445

509-517

1548

4436310

Human adenylosuccinate synthetase. Partial purification, kinetic and regulatory properties of the enzyme from placenta

1974

Van der Weyden, M.B.; Kelly, W.N.

J. Biol. Chem.

249

7282-7289

1549

4809527

Purification of adenylosuccinate synthetase from rabbit skeletal muscle

1974

Muirhead, K.M.; Bishop, S.H.

J. Biol. Chem.

249

459-464

1550

4708672

Regulation of the biosynthesis of purine nucleotides in Schizosaccharomyces pombe. II. Kinetic studies of adenylosuccinate synthetase

1973

Nagy, M.; Djembo-Taty, M.; Heslot, H.

Biochim. Biophys. Acta

309

1-10

1551

8790347

The mode of action and the structure of a herbicide in the complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase

1996

Fonne-Pfister, R.; Chemla, P.; Ward, E.; Girardet, M.; Kreuz, K.E.; Honzatko, R.B.; Fromm, H.J.; Schär, H.P.; Grutter, M.G.; Cowan-Jacob, S.W.

Proc. Natl. Acad. Sci. USA

93

9431-9436

1552

1989999

Purification and cDNA-derived sequence of adenylosuccinate synthetase from Dictyostelium discoideum

1991

Wiesmuller, L.; Wittbrodt, J.; Noegel, A.A.; Schleicher, M.

J. Biol. Chem.

266

2480-2485

1553

7490761

Refined crystal structure of unligated adenylosuccinate synthetase from Escherichia coli

1995

Silva, M.M.; Poland, B.W.; Hoffman, C.R.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

254

431-446

1554

9000627

Crystal structures of adenylosuccinate synthetase from Escherichia coli complexed with GDP, IMP hadacidin, NO3-, and Mg2+

1996

Poland, B.W.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

264

1013-1027

1555

8703905

Involvement of arginine 143 in nucleotide substrate binding at the active site of adenylosuccinate synthetase from Escherichia coli

1996

Moe, O.A.; Baker-Malcolm, J.F.; Wang, W.; Kang, C.; Fromm, H.J.; Colman, R.F.

Biochemistry

35

9024-9033

1556

8179335

Characterization of the putative GTP-binding site residues of Escherichia coli adenylosuccinate synthetase by site-directed mutagenesis

1994

Kang, C.; Fromm, H.J.

Arch. Biochem. Biophys.

310

475-480

1557

8961938

Refined crystal structure of adenylsuccinate synthetase from Escherichia coli complexed with hydantocidin 5'-phosphate, GDP, HPO42-, Mg2+, and hadacidin

1996

Poland, B.W.; Lee, S.F.; Subramanian, M.V.; Siehl, D.L.; Anderson, R.J.; Fromm, H.J.; Honzatko, R.B.

Biochemistry

35

15753-15759

1558

9182542

Entrapment of 6-thiophosphoryl-IMP in the active site of crystalline adenylosuccinate synthetase from Escherichia coli

1997

Poland, B.W.; Bruns, C.; Fromm, H.J.; Honzatko, R.B.

J. Biol. Chem.

272

15200-15205

1559

9115248

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