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• • Molecular Structure
  • Sum Formula
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  • Synonyms
  • InChIKey
  • Pathways
• Roles as Enzyme Ligand
• • In Vivo Substrate
  • In Vivo Product
  • Substrate
  • Product
  • Cofactor
  • Activator
  • Inhibitor
  • Metals and Ions
  • 3D Structure (PDB)
• Enzyme Kinetic Parameters
• • k_cat Value (Turnover Number)
  • K_M Value
  • K_i Value
  • IC₅₀ Value
• References & Links
• • References
  • Links

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Ligand 7-methylguanosine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

7-methylguanosine + phosphate = 7-methylguanine + alpha-D-ribose 1-phosphate

759175, 759339

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

7-methylguanine + alpha-D-ribose 1-phosphate = 7-methylguanosine + phosphate

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-

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

7-methylguanosine + phosphate = 7-methylguanine + alpha-D-ribose 1-phosphate

489659, 489683, 701906, 489685, 662986, 689267, 721842, 701915, 676239, 672404, 489711, 673191, 689879, 721756, 736083, 759175, 759339

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2.7.1.77

4-nitrophenyl phosphate + 7-methylguanosine = 4-nitrophenol + 7-methylguanosine 5'-phosphate

641995

-

3.2.2.1

7-methyl guanosine + H2O = D-ribose + 7-methyl guanine

669883, 698781

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3.2.2.1

7-methylguanosine + H2O = ?

714225

-

3.2.2.1

7-methylguanosine + H2O = D-ribose + 7-methylguanine

752135

-

3.2.2.1

3 entries

3.2.2.2

7-methylguanosine + H2O = 7-methylguanine + D-ribose

683973

-

3.2.2.25

7-methylguanosine + H2O = 7-methylguanine + D-ribose

137101

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.2.1

7-methylguanine + alpha-D-ribose 1-phosphate = 7-methylguanosine + phosphate

-

-

3.1.3.5

7-methylguanosine monophosphate + H2O = 7-methylguanosine + phosphate

-

4nv0, 3D-view

3.1.3.91

N7-methyl-GDP + H2O = N7-methyl-guanosine + 2 phosphate

-

-

3.1.3.91

N7-methyl-GMP + H2O = N7-methyl-guanosine + phosphate

-

-

3.1.3.91

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (7 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (7 entries)

EC NUMBER

ENZYME 3D STRUCTURE

2.7.7.19

1eqa, 3D-view

2.7.7.19

4dcg, 3D-view

2.7.7.19

1eqa, 3D-view

2.7.7.19

4dcg, 3D-view

2.7.7.19

1eqa, 3D-view

2.7.7.19

4dcg, 3D-view

2.7.7.19

6 entries

3.1.3.5

4nv0, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (14 results)

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Show Turnover Number (14 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.4.2.1

6.23

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

9.2

-

presence of 50 mM phosphate, pH 7.0

701906

2.4.2.1

20.4

-

presence of 50 mM phosphate, pH 7.0

701906

2.4.2.1

23

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

24.7

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

73.1

-

presence of 50 mM phosphate, pH 7.0

701906

3.2.2.1

1.07

-

wild type enzyme, in 50 mM potassium phosphate buffer, at 25°C and pH 7.0

698781

3.2.2.1

1.09

-

wild-type, pH 7.5, 25°C

752135

3.2.2.1

1.98

-

mutant C253A, ApH 7.5, 25°C

752135

3.2.2.1

2.4

-

mutant C42A, pH 7.5, 25°C

752135

3.2.2.1

3.4

-

wild-type, pH 7.0, 35°C

669883

3.2.2.1

5.2

-

at pH 7.0 and 5°C

714225

3.2.2.1

13.2

-

mutant R252A, pH 7.0, 35°C

669883

3.2.2.1

13.6

-

mutant D40A, pH 7.0, 35°C

669883

2.4.2.1

6 entries

3.2.2.1

8 entries

K_M Value (23 results)

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Show KM Value (23 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.2.1

0.0147

-

-

489683

2.4.2.1

0.015

-

-

489685, 489711

2.4.2.1

0.016

-

-

673191

2.4.2.1

0.0168

-

pH 7.0, 25°C, recombinant enzyme

689879

2.4.2.1

0.0168

-

wild-type, pH not specified in the publication, temperature not specified in the publication

721842

2.4.2.1

0.0264

-

25°C, pH 7.0

672404

2.4.2.1

0.05

-

mutant F159W, pH not specified in the publication, temperature not specified in the publication

721842

2.4.2.1

0.0544

-

pH 7.0, 25°C

759175

2.4.2.1

0.07

-

mutant F200W, pH not specified in the publication, temperature not specified in the publication

721842

2.4.2.1

0.6

-

-

489683, 489711

2.4.2.1

9.2

-

presence of 50 mM phosphate, pH 7.0

701906

2.4.2.1

12.5

-

presence of 50 mM phosphate, pH 7.0

701906

2.4.2.1

13

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

13.9

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

16.3

-

presence of 100 mM phosphate, pH 7.0

701906

2.4.2.1

39.3

-

presence of 50 mM phosphate, pH 7.0

701906

3.2.2.1

0.0005

-

wild type enzyme, in 50 mM potassium phosphate buffer, at 25°C and pH 7.0

698781

3.2.2.1

0.0021

-

wild-type, pH 7.0, 35°C

669883

3.2.2.1

0.0024

-

mutant R252A, pH 7.0, 35°C

669883

3.2.2.1

0.008

-

mutant D40A, pH 7.0, 35°C

669883

3.2.2.1

0.037

-

wild-type, pH 7.5, 25°C

752135

3.2.2.1

0.051

-

mutant C253A, ApH 7.5, 25°C

752135

3.2.2.1

0.053

-

mutant C42A, pH 7.5, 25°C

752135

2.4.2.1

16 entries

3.2.2.1

7 entries

References & Links

Literature References (24)

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Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

137101

-

N-methyl nucleosidase from tea leaves

1988

Negishi, O.; Ozawa, T.; Imagawa, H.

Agric. Biol. Chem.

52

169-175

489659

1576149

Formycins A and B and some analogues: selective inhibitors of bacterial (Escherichia coli) purine nucleoside phosphorylase

1992

Bzowska, A.; Kulikowska, E.; Shugar, D.

Biochim. Biophys. Acta

1120

239-247

489683

3132457

Purine nucleoside phosphorylase. Structure-activity relationships for substrate and inhibitor properties of N-1-, N-7-, and C-8-substituted analogues; differentiation of mammalian and bacterial enzymes with N-1-methylinosine and guanosine

1988

Bzowska, A.; Kulikowska, E.; Darzynkiewicz, E.; Shugar, D.

J. Biol. Chem.

263

9212-9217

489685

3098294

Properties of two unusual, and fluorescent, substrates of purine-nucleoside phosphorylase: 7-methylguanosine and 7-methylinosine

1986

Kulikowska, E.; Bzowska, A.; Wierzchowski, J.; Shugar, D.

Biochim. Biophys. Acta

874

355-363

489711

11337031

Purine nucleoside phosphorylases: properties, functions, and clinical aspects

2000

Bzowska, A.; Kulikowska, E.; Shugar, D.

Pharmacol. Ther.

88

349-425

641995

3013235

Nucleoside phosphotransferase from malt sprouts. I. Isolation, characterization and specificity of the enzyme

1986

Billich, A.; Stockhowe, U.; Witzel, H.

Biol. Chem. Hoppe-Seyler

367

267-278

662986

14565467

Interactions of potent multisubstrate analogue inhibitors with purine nucleoside phosphorylase from calf spleen--kinetic and spectrofluorimetric studies

2003

Iwanow, M.; Magnowska, L.; Yokomatsu, T.; Shibuya, S.; Bzowska, A.

Nucleosides Nucleotides Nucleic Acids

22

1567-1570

669883

16630632

Transition-state complex of the purine-specific nucleoside hydrolase of T. vivax: enzyme conformational changes and implications for catalysis

2006

Versees, W.; Barlow, J.; Steyaert, J.

J. Mol. Biol.

359

331-346

672404

16631420

Probing the mechanism of purine nucleoside phosphorylase by steady-state kinetic studies and ligand binding characterization determined by fluorimetric titrations

2006

Wielgus-Kutrowska, B.; Bzowska, A.

Biochim. Biophys. Acta

1764

887-902

673191

17348834

Purine nucleoside phosphorylase: a potential target for the development of drugs to treat T-cell- and apicomplexan parasite-mediated diseases

2007

Silva, R.G.; Nunes, J.E.; Canduri, F.; Borges, J.C.; Gava, L.M.; Moreno, F.B.; Basso, L.A.; Santos, D.S.

Curr. Drug Targets

8

413-422

676239

16247973

Kinetic properties of Cellulomonas sp. purine nucleoside phosphorylase with typical and non-typical substrates: implications for the reaction mechanism

2005

Wielgus-Kutrowska, B.; Bzowska, A.

Nucleosides Nucleotides Nucleic Acids

24

471-476

683973

16820181

Calcium-stimulated guanosine--inosine nucleosidase from yellow lupin (Lupinus luteus)

2006

Szuwart, M.; Starzynska, E.; Pietrowska-Borek, M.; Guranowski, A.

Phytochemistry

67

1476-1485

689267

18066912

Interactions of calf spleen purine nucleoside phosphorylase with formycin B and its aglycone - spectroscopic and kinetic studies

2007

Wierzchowski, J.; Iwanska, B.; Bzowska, A.; Shugar, D.

Nucleosides Nucleotides Nucleic Acids

26

849-854

689879

18585465

Overexpression, purification and characterization of functional calf purine nucleoside phosphorylase (PNP)

2008

Breer, K.; Girstun, A.; Wielgus-Kutrowska, B.; Staro?, K.; Bzowska, A.

Protein Expr. Purif.

61

122-130

698781

18519562

A flexible loop as a functional element in the catalytic mechanism of nucleoside hydrolase from Trypanosoma vivax

2008

Vandemeulebroucke, A.; De Vos, S.; Van Holsbeke, E.; Steyaert, J.; Versees, W.

J. Biol. Chem.

283

22272-22282

701906

18938130

Effect of the phosphate substrate on drug-inhibitor binding to human purine nucleoside phosphorylase

2008

Todorova, N.A.; Schwarz, F.P.

Arch. Biochem. Biophys.

480

122-131

701915

19416718

Substrate specificity and kinetic mechanism of purine nucleoside phosphorylase from Mycobacterium tuberculosis

2009

Ducati, R.G.; Santos, D.S.; Basso, L.A.

Arch. Biochem. Biophys.

486

155-164

714225

20825170

Structure and mechanism of the 6-oxopurine nucleosidase from Trypanosoma brucei brucei

2010

Vandemeulebroucke, A.; Minici, C.; Bruno, I.; Muzzolini, L.; Tornaghi, P.; Parkin, D.W.; Versees, W.; Steyaert, J.; Degano, M.

Biochemistry

49

8999-9010

721756

21672603

Validation of the catalytic mechanism of Escherichia coli purine nucleoside phosphorylase by structural and kinetic studies

2011

Mikleusevic, G.; Stefanic, Z.; Narczyk, M.; Wielgus-Kutrowska, B.; Bzowska, A.; Luic, M.

Biochimie

93

1610-1622

721842

23040896

Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state

2012

Wielgus-Kutrowska, B.; Breer, K.; Hashimoto, M.; Hikishima, S.; Yokomatsu, T.; Narczyk, M.; Dyzma, A.; Girstun, A.; Staro?, K.; Bzowska, A.

Bioorg. Med. Chem.

20

6758-6769

736083

24785777

Homooligomerization is needed for stability: a molecular modelling and solution study of Escherichia coli purine nucleoside phosphorylase

2014

Bertosa, B.; Mikleusevic, G.; Wielgus-Kutrowska, B.; Narczyk, M.; Hajnic, M.; Lescic Asler, I.; Tomic, S.; Luic, M.; Bzowska, A.

FEBS J.

281

1860-1871

752135

28218438

Structural and biochemical characterization of the nucleoside hydrolase from C. elegans reveals the role of two active site cysteine residues in catalysis

2017

Singh, R.K.; Steyaert, J.; Versees, W.

Protein Sci.

26

985-996

759175

29430816

Helicobacterpylori purine nucleoside phosphorylase shows new distribution patterns of open and closed active site conformations and unusual biochemical features

2018

Narczyk, M.; Bertosa, B.; Papa, L.; Vukovic, V.; Lescic Asler, I.; Wielgus-Kutrowska, B.; Bzowska, A.; Luic, M.; Stefanic, Z.

FEBS J.

285

1305-1325

759339

28336275

Structural characterization of purine nucleoside phosphorylase from human pathogen Helicobacter pylori

2017

Stefanic, Z.; Mikleusevic, G.; Luic, M.; Bzowska, A.; Lescic Asler, I.

Int. J. Biol. Macromol.

101

518-526

Links to other databases for 7-methylguanosine

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Show Links (1 entry)

ChEBI

PubChem

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