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Ligand 2,3-diphosphoglycerate

Basic Ligand Information

Molecular Structure

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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

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

5.4.2.11

2-phospho-D-glycerate + 2,3-bisphosphoglycerate = 3-phospho-D-glycerate + 2,3-bisphosphoglycerate

649656

-

5.4.2.4

2,3-Diphosphoglycerate = ?

3308, 3306

-

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

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.4.61

cyclic 2,3-bisphosphoglycerate + H2O = 2,3-diphosphoglycerate

-

-

5.4.2.11

2-phospho-D-glycerate + 2,3-bisphosphoglycerate = 3-phospho-D-glycerate + 2,3-bisphosphoglycerate

649656

-

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.3.2

2,3-bisphosphoglycerate + H2O = ?

714280

-

3.1.3.2

2,3-diphosphoglycerate + H2O = ?

134766, 134771, 134800, 134754, 134743

-

3.1.3.2

2 entries

3.1.3.20

2,3-diphosphoglycerate + H2O = ?

81023

-

3.1.3.23

2,3-diphosphoglycerate + H2O = ?

94727

-

3.1.3.25

2,3-diphosphoglycerate + H2O = ?

114220

-

3.1.3.28

2,3-bisphosphoglycerate + H2O = ?

81037

-

3.1.3.60

2,3-diphosphoglycerate + H2O = ?

134800, 646421

-

3.1.3.62

2,3-bisphosphoglycerate + H2O = 2-phosphoglycerate + phosphate

694894

-

5.4.2.11

2-phospho-D-glycerate + 2,3-bisphosphoglycerate = 3-phospho-D-glycerate + 2,3-bisphosphoglycerate

649656

-

5.4.2.4

2,3-Diphosphoglycerate = ?

3308, 3306

-

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.4.61

cyclic 2,3-bisphosphoglycerate + H2O = 2,3-diphosphoglycerate

-

-

5.4.2.11

2-phospho-D-glycerate + 2,3-bisphosphoglycerate = 3-phospho-D-glycerate + 2,3-bisphosphoglycerate

649656

-

5.4.2.4

1,3-Diphosphoglycerate = 2,3-Diphosphoglycerate

3313, , 3319, 3318

-

Enzyme Cofactor/Cosubstrate (2 results)

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Show Cofactor (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

5.4.2.11

required to prime the reaction in an initial phosphorylation step

649656

-

5.4.2.11

dependent on 2,3-bisphosphoglyceric acid for activity

715964

-

5.4.2.11

2 entries

Activator in Enzyme-catalyzed Reactions (29 results)

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Show Activating Compound (29 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.44

activates both isoenzymes up to 200% of their original activity

286866

-

1.2.7.6

stimulates

644692

-

2.3.1.101

the 1 M 2,3-diphosphoglycerate the enzyme is highly active

726828

-

2.4.1.11

low concentrations

488418

-

2.7.7.27

activation

643134, 643117

-

2.7.7.27

actvation of ADP-glucose synthesis

643117

-

2.7.7.27

allosteric activator

643134

-

2.7.7.27

no activation

643120, 643116, 643123

-

2.7.7.27

4 entries

3.1.3.48

activation

94974

-

3.1.3.5

-

677295, 665608, 660724, 714967

-

3.1.3.5

activates cytosolic 5'-nucleotidase II

716355

-

3.1.3.5

allosteric activation

715932

-

3.1.3.5

activation

95025

-

3.1.3.5

activation of cytosolic enzyme

95072

-

3.5.4.27

optimally active at 0.6 M, about 5500 U/mg

755911

-

3.5.4.27

the potassium salts of 2,3-bisphosphoglycerate stimulates cyclohydrolase activity

726828

-

3.5.4.27

the activity increases with increasing 2,3-diphosphoglycerate concentrations from 30 U/mg up to a specific activity of 7,500 U/mg. The maximal activity is reached at a 2,3-diphosphoglycerate concentration of 0.75 M. At higher concentrations, the activity decreases

726828

-

5.4.2.11

-

652877, 649656, 651088, 652799, 3216, 649101, 652790

-

5.4.2.11

dependent on

726607

-

5.4.2.11

-

3260, 3213, 3217, 3240, 3219, 3221, 3229

-

5.4.2.11

Km: 0.005, wild-type enzyme, Km: 0.003, mutant K246G, Km: 0.048, mutant S11G

3231

-

5.4.2.11

Km: 0.008 mM

3253

-

5.4.2.11

Km: 0.0081, wild-type enzyme, Km: 0.087, H181A-mutant

3230

-

5.4.2.11

Km: 0.01 mM

3253

-

5.4.2.11

Km: 0.082 mM

3254

-

5.4.2.12

strictly required, Km value 0.017 mM

679715

-

5.4.2.12

-

3239, 3241

-

5.4.2.12

no cofactor

3249, 3250, 3252, 3259, 3237, 3226, 3222

-

5.4.2.12

plant enzyme does not require a cofactor

3213

-

3.1.3.5

5 entries

3.5.4.27

3 entries

5.4.2.11

8 entries

5.4.2.12

4 entries

Inhibitor in Enzyme-catalyzed Reactions (38 results)

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Show Inhibitors (38 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.49

-

287016

-

1.2.1.12

-

287920, 287945

-

1.5.1.30

-

392188

-

2.4.1.1

5 mM, 30% inhibition

488264

-

2.4.1.11

high concentrations

488418

-

2.5.1.54

-

639749

-

2.7.1.1

feedback regulation. The phosphorylation of glucose is the reaction whose rate controls that of the formation of diphosphoglyceric acid. It is therefore clear that this phosphorylation by diphosphoglyceric acid serves as the automatic regulation of the former by the latter

758866, 758986

-

2.7.1.1

-

640251

-

2.7.1.1

hexokinase III

640241

-

2.7.1.106

0.2 mM, strong inhibitor

674867

-

2.7.1.106

-

640348, 640350

-

2.7.1.106

strong, liver

640349

-

2.7.1.1

3 entries

2.7.1.106

3 entries

2.7.1.11

-

640467

-

2.7.1.127

-

640747

-

2.7.1.40

-

641516, 641526, 641576

-

2.7.11.15

inhibits in the millimolar range, IC50: 1.1 mM with rhodopsin as substrate; weak

645003

-

2.7.11.15

weak

490911

-

2.7.2.3

-

642266, 642289

-

2.7.2.3

competitive to 3-phospho-D-glycerate and MgATP2-

642253

-

2.7.2.3

noncompetitive with respect to 1,3-diphosphoglycerate

642275

-

2.7.6.1

-

642720

-

2.7.6.1

30% inhibition at 1 mM; competitive to D-ribose 5-phosphate

642717

-

2.7.6.1

at 1 mM, inhibition of isoenzyme PRSI and PRSII, at 1-10 mM, stimulation of isoenzyme PRSI

642719

-

2.7.6.1

competitive to D-ribose 5-phosphate; inhibition of the erythrocyte enzyme

642710

-

2.7.6.1

inhibition, even in the presence of stabilizing agents such as albumin, EDTA and dithiothreitol

642730

-

2.7.11.15

2 entries

2.7.2.3

3 entries

2.7.6.1

5 entries

3.1.3.36

-

134823

-

3.1.3.56

-

646374, 646376, 646378, 646382, 646391, 646392, 646394, 646396, 646398

-

3.1.3.56

competitive with D-myo-inositol 1,4,5-trisphosphate

646372

-

3.1.3.56

2 entries

3.1.3.86

-

714011

-

3.1.4.61

product inhibition

760553

-

3.5.4.6

ATP counteracts inhibition

209676

-

3.6.1.7

-

246781

-

3.6.1.7

competitive inhibition, Ki erythrocyte enzyme: 0.41 mM, Ki skeletal muscle enzyme: 3.74 mM

246775

-

3.6.1.7

erythrocyte isoenzyme, competitive inhibition, Ki: 0.24 mM

246792

-

3.6.1.7

heart enzyme, 2 mM: 12% inhibition, substrate: 1,3-diphosphoglycerate

246781

-

3.6.1.7

4 entries

4.3.1.1

-

649266

-

5.4.2.2

-

3275, 3285, 3287

-

5.4.2.4

product inhibition

3323

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

5.4.2.4

0.0037

-

wild-type

3306

5.4.2.4

0.00623

-

mutant C22S

3306

5.4.2.4

0.00845

-

mutant S23G

3306

5.4.2.4

0.152

-

mutant C22T

3306

5.4.2.4

4 entries

K_M Value (14 results)

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Show KM Value (14 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.3.2

0.09

-

-

134800

3.1.3.28

27

-

-

81037

3.1.3.60

0.5

-

25°C, pH 5.6

646421

3.1.3.62

0.61

-

recombinant enzyme, at 37°C

694894

5.4.2.4

0.0024

-

presence of activator 2-phosphoglycolate

3318

5.4.2.4

0.0028

-

absence of activator 2-phosphoglycolate

3318

5.4.2.4

0.0094

-

peak II enzyme

3319

5.4.2.4

0.0096

-

peak I enzyme

3319

5.4.2.4

0.0222

-

peak III enzyme

3319

5.4.2.4

0.11

-

-

3307

5.4.2.4

0.182

-

mutant S23G

3306

5.4.2.4

0.281

-

mutant C22S

3306

5.4.2.4

0.3

-

wild-type

3306

5.4.2.4

0.583

-

mutant C22T

3306

5.4.2.4

10 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

2.7.1.1

5

-

hexokinase III, at 30°C, pH 7.2

640241

2.7.1.1

14

-

at 30°C, pH 8.1

640251

2.7.2.3

0.35

-

pH 7.5, 20°C, versus 3-phospho-D-glycerate

642289

2.7.2.3

2.3

-

versus MgATP2-

642253

2.7.2.3

3.8

-

versus 3-phospho-D-glycerate

642253

2.7.1.1

2 entries

2.7.2.3

3 entries

3.1.3.56

0.35

-

-

646372

4.3.1.1

1.1

-

-

649266

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.7.11.15

1.1

-

inhibits in the millimolar range, IC50: 1.1 mM with rhodopsin as substrate

645003

References & Links

Literature References (119)

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Show Reference (119 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

3213

6255773

The enzymology of 2,3-bisphosphoglycerate

1980

Rose, Z.B.

Adv. Enzymol. Relat. Areas Mol. Biol.

51

211-253

3216

9512715

The 2.3 A X-ray crystal structure of S. cerevisiae phosphoglycerate mutase

1998

Rigden, D.J.; Alexeev, D.; Phillips, S.E.; Fothergill-Gilmore, L.A.

J. Mol. Biol.

276

449-459

3217

9365161

Phosphoglycerate mutase, 2,3-bisphosphoglycerate phosphatase and creatine kinase activity and isoenzymes in human brain tumors

1997

Durany, N.; Joseph, J.; Cruz-Sanchez, F.F.; Carreras, J.

Br. J. Cancer

76

1139-1149

3219

8736982

The reaction of phosphoglycerate mutase from Schizosaccharomyces pombe with diethylpyrocarbonate

1996

Price, R.M.; Nairn, J.; Price, N.C.; Fothergill-Gilmore, L.A.

Biochem. Soc. Trans.

24

324S

3221

8765231

Phosphoglycerate mutase from Schizosaccharomyces pombe: development of an expression system and characterisation of three histidine mutants of the enzyme

1996

Nairn, J.; Price, N.C.; Kelly, S.M.; Rigden, D.; Fothergill-Gilmore, L.A.; Krell, T.

Biochim. Biophys. Acta

1296

69-75

3222

8931352

Lily cofactor-independent phosphoglycerate mutase: purification, partial sequencing and immunolocalization

1996

Wang, J.L.; Walling, L.L.; Jauh, G.Y.; Gu, Y.Q.; Lord, E.M.

Planta

200

343-352

3226

8093040

Isolation and characterization of cofactor-independent phosphoglycerate mutase gene from maize

1994

Perez de la Ossa, P.; Grana, X.; Ruiz-Lozano, P.; Climent, F.

Biochem. Biophys. Res. Commun.

203

1204-1209

3229

1530847

Phosphoglycerate mutase from Streptomyces coelicolor A3(2): purification and characterization of the enzyme and cloning and sequence analysis of the gene

1992

White, P.J.; Nairn, J.; Price, N.C.; Nimmo, H.G.; Coggins, J.R.; Hunter, I.S.

J. Bacteriol.

174

434-440

3230

1386023

Development of a mutagenesis, expression and purification system for yeast phosphoglycerate mutase

1992

White, M.F.; Fothergill-Gilmore, L.A.

Eur. J. Biochem.

207

709-714

3231

2165932

Mutase versus synthase: the phosphoglycerate mutase family studied by protein engineering

1990

White, M.; Fothergill-Gilmore L.A.

Biochem. Soc. Trans.

18

257

3237

-

Cofactor-independent monophosphoglycerate mutase

1988

McAleese, S.M.; Dunbar, B.; Kay, I.; Fothergill-Gilmore, L.A.

Biochem. Soc. Trans.

16

558-559

3239

-

Co-factor-independent phosphoglycerate mutases

1987

Johnson, C.M.; Gore, M.J.; Price, N.C.

Biochem. Soc. Trans.

15

878

3240

-

How similar are the phosphoglycerate mutases from yeast and rabbit muscle?

1987

Johnson, C.M.; Price, N.C.

Biochem. Soc. Trans.

15

247-248

3241

3026343

Isolation and properties of the glycolytic enzymes from Zymomonas mobilis. The five enzymes from glyceraldehyde-3-phosphate dehydrogenase through to pyruvate kinase

1986

Pawluk, A.; Scopes, R.K.; Griffiths-Smith, K.

Biochem. J.

238

275-281

3249

33959

Purification and properties of phosphoglycerate phosphomutase from spores and cells of Bacillus megaterium

1979

Singh, R.P.; Setlow, P.

J. Bacteriol.

137

1024-1027

3250

33963

Purification and properties of the manganese-dependent phosphoglycerate mutase of Bacillus subtilis

1979

Watabe, K.; Freese, E.

J. Bacteriol.

137

773-778

3252

19039

Phosphoglycerate mutase from wheat germ. Studies with isotopically labeled 3-phospho-D-glycerates showing that the catalyzed reaction is intramolecular

1977

Gatehouse, J.A.; Knowles, J.R.

Biochemistry

16

3045-3052

3253

10346

Purification and characterization of phosphoglycerate mutase from methanol-grown Hyphomicrobium X and Pseudomonas AM1

1976

Hill, B.; Attwood, M.M.

J. Gen. Microbiol.

96

185-193

3254

10303

Isolation and partial characterization of monophosphoglycerate mutase from human erythrocytes

1976

Sheibley, R.H.; Hass, L.F.

J. Biol. Chem.

251

6699-6704

3259

-

Phosphoglycerate mutase from wheat germ (2,3-PGA-independent)

1975

Grisolia, S.; Carreras, J.

Methods Enzymol.

42

429-435

3260

166274

Phosphoglycerate kinase, phosphoglyceromutase from Escherichia coli

1975

D'Alessio, G.; Josse, J.

Methods Enzymol.

42

139-144

3275

2149596

Purification and partial characterization of the phosphoglucomutase isozymes from human placenta

1990

Fazi, A.; Piacentini, M.P.; Piatti, E.; Accorsi, A.

Prep. Biochem.

20

219-240

3285

-

Purification and properties of beef liver phosphoglucomutase

1976

Chiba, H.; Ueda, M.; Hirose, M.

Agric. Biol. Chem.

40

2423-2431

3287

31356

Phosphoglucomutase from potato tubers. Chemical and catalytical properties

1978

Takamiya, S.; Fukui, T.

J. Biochem.

84

569-574

3306

9162026

Critical Role of Human bisphosphoglycerate mutase Cys22 in the phosphatase activator-binding site

1997

Ravel, P.; Craescus, C.T.; Arous, N.; Rosa, J.; Garel, M.C.

J. Biol. Chem.

272

14045-14050

3307

2145041

Human bisphosphogycerate mutase expressed in E. coli: purification, characterization and structure studies

1990

Calcin, M.C.; Blouquit, Y.; Garel, M.C.; Cohen-Solal, M.; Rosa, J.; Rosa, R.

Biochimie

72

337-343

3308

-

Natural and artificial mutants of the human 2,3-bisphosphoglycerate as a tool for the evaluation of structure-function relationship

1990

Garel, M.C.; Lemarchandel, M.O.; Prehu, M.O.; Calvin, M.C.; Arous, N.; Rosa, R.; Rosa, J.

Biomed. Biochim. Acta

49

166-171

3313

4694722

The phosphorylation of diphosphoglycerate mutase

1973

Rose, Z.B.; Whalen, R.G.

J. Biol. Chem.

248

1513-1519

3318

199431

Purification and properties of 2,3-bisphosphoglycerate phosphatase-mutase from erythrocytes of day-old chicks

1977

Harkness, D.R.; Isaacks, R.E.; Roth, S.C.

Eur. J. Biochem.

78

343-351

3319

163190

Purification of bisphosphoglyceromutase, 2,3-bisphosphoglycerate phosphatase and phosphoglyceromutase from human erthrocytes. Three enzyme activities in one protein

1975

Sasaki, R.; Ikura, K.; Sugimoto, E.; Chiba, H.

Eur. J. Biochem.

50

581-593

3323

187124

The purification and kinetic properties of bisphosphoglycerate synthase from horse red blood cells

1976

Rose, Z.B.; Dube, S.

Arch. Biochem. Biophys.

177

284-292

81023

6271379

2-Phosphoglycerate phosphatase and serine biosynthesis in Veillonella alcalescens

1981

Pestka, J.J.; Delwiche, E.A.

Can. J. Microbiol.

27

808-814

81037

14243760

Enzymic dephosphorylation of adenosine diphosphate phosphoglyceric acid

1964

Zancan, G.T.; Recondo, E.F.; Leloir, L.F.

Biochim. Biophys. Acta

92

125-131

94727

7622485

Purification and characterization of a small membrane-associated sugar phosphate phosphatase that is allosterically activated by HPr(Ser(P)) of the phosphotransferase system in Lactococcus lactis

1995

Ye, J.J.; Saier, M.H.

J. Biol. Chem.

270

16740-16744

94974

2424449

Partial purification and characterization of phosphotyrosyl-protein phosphatase(s) from human erythrocyte cytosol

1986

Clari, G.; Brunati, A.M.; Moret, V.

Biochem. Biophys. Res. Commun.

137

566-572

95025

2848805

High Km soluble 5'-nucleotidase from human placenta. Properties and allosteric regulation by IMP and ATP

1988

Spychala, J.; Madrid-Marina, V.; Fox, I.H.

J. Biol. Chem.

263

18759-18765

95072

9687019

Identification, separation and characterization of two forms of cytosolic 5'-nucleotidase/nucleoside phosphotransferase in calf thymus

1998

Pesi, R.; Baiocchi, C.; Allegrini, S.; Moretti, E.; Sgarrella, F.; Camici, M.; Tozzi, M.G.

Biol. Chem.

379

699-704

114220

6272635

Studies on avian erythrocyte metabolism: purification and properties of myo-inositol 1-phosphatase from chick erythrocytes

1981

Roth, S.C.; Harkness, D.R.; Isaacks, R.E.

Arch. Biochem. Biophys.

210

465-473

134743

736900

Purification and some properties of tartrate-sensitive acid phosphatase from rabbit kidney cortex

1978

Helwig, J.J.; Farooqui, A.A.; Bollack, C.; Mandel, P.

Biochem. J.

175

321-329

134754

-

Acid phosphatase isoenzymes of Xenopus laevis tadpole tails. Separation and partial characterization

1973

Filburn, C.R.

Arch. Biochem. Biophys.

159

683-693

134766

4235424

Properties of an acid phosphatase in Escherichia coli

1968

Hafkenscheid, J.C.M.

Biochim. Biophys. Acta

167

582-589

134771

14408027

Purification and properties of a nonspecific acid phosphatase from wheat germ

1960

Joyce, B.K.; Grisolia, S.

J. Biol. Chem.

235

2278-2280

134800

1897950

Purification, characterization, and subcellular localization of an acid phosphatase from black mustard cell-suspension cultures: comparison with phosphoenolpyruvate phosphatase

1991

Duff, S.M.G.; Lefebvre, D.D.; Plaxton, W.C.

Arch. Biochem. Biophys.

286

226-232

134823

7508913

Purification of two immunologically related phosphatidylinositol-(4,5)-bisphosphate phosphatases from bovine brain cytosol

1994

Palmer, F.B.S.C.; Theolis, R.; Cook, H.W.; Byers, D.M.

J. Biol. Chem.

269

3403-3410

209676

4828847

The kinetic properties of adenylate deaminase from human erythrocytes

1978

Lian, C.; Harkness, D.R.

Biochim. Biophys. Acta

341

27-40

246775

3026468

A new acylphosphatase isoenzyme from human erythrocytes: purification, characterization, and primary structure

1986

Liguri, G.; Camici, G.; Manao, G.; Cappugi, G.; Nassi, P.; Modesti, A.; Ramponi, G.

Biochemistry

25

8089-8094

246781

237200

1,3-Diphosphoglycerate phosphatase

1975

Ramponi, G.

Methods Enzymol.

42C

409-426

246792

8262761

Purification, kinetic properties and primary structure of bovine erythrocyte acylphosphatase

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