print visible entries

print all entries

Ligand 7-cyano-7-deazaguanine

Basic Ligand Information

Molecular Structure

Related pathways

Show all BRENDA pathways known for 7-cyano-7-deazaguanine

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

top print hide

Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.7.1.13

2-amino-5-cyanopyrrolo[2,3-d]pyrimidin-4-one + 2 NADPH + 2 H+ = 2-amino-5-amino-methyl-pyrrolo[2,3-d]pyrimidin-4-one + 2 NADP+

724767

4FGC, 3D-view

1.7.1.13

7-cyano-7-deazaguanine + 2 NADPH + 2 H+ = 7-aminomethyl-7-deazaguanine + 2 NADP+

765048, 764418

4FGC, 3D-view

1.7.1.13

7-cyano-7-deazaguanine + 2 NADPH + 2 H+ = queuine + 2 NADP+

660634, 663244

4FGC, 3D-view

2.4.2.48

guanine15 in tRNA + 7-cyano-7-carbaguanine = 7-cyano-7-carbaguanine15 in tRNA + guanine

719802, 722604, 728740

-

2.4.2.48

guanine15 in tRNA + 7-cyano-7-deazaguanine = 7-cyano-7-deazaguanine15 in tRNA + guanine

738326

-

1.7.1.13

3 entries

2.4.2.48

2 entries

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

top print hide

Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.20

7-carboxy-7-carbaguanine + NH3 + ATP = 7-cyano-7-carbaguanine + ADP + phosphate + H2O

-

-

6.3.4.20

7-carboxy-7-carbaguanine + NH3 + ATP = 7-cyano-7-carbaguanine + AMP + diphosphate + H2O

-

-

6.3.4.20

2 entries

Substrate in Enzyme-catalyzed Reactions (18 results)

top print hide

Show Substrate (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.7.1.13

2-amino-5-cyanopyrrolo[2,3-d]pyrimidin-4-one + 2 NADPH + 2 H+ = 2-amino-5-amino-methyl-pyrrolo[2,3-d]pyrimidin-4-one + 2 NADP+

724767

4FGC, 3D-view

1.7.1.13

7-cyano-7-carbaguanine + 2 NADPH + 2 H+ = 7-aminomethyl-7-carbaguanine + 2 NADP+

741484, 742231, 742900, 743107

4FGC, 3D-view

1.7.1.13

7-cyano-7-deazaguanine + 2 NADPH + 2 H+ = 7-aminomethyl-7-deazaguanine + 2 NADP+

765048, 764418

4FGC, 3D-view

1.7.1.13

7-cyano-7-deazaguanine + 2 NADPH + 2 H+ = queuine + 2 NADP+

660634, 663244, 662984, 662983, 712770

4FGC, 3D-view

1.7.1.13

7-cyano-7-deazaguanine + NADPH + H+ = queuine + NADP+ + H+

724879

4FGC, 3D-view

2.4.2.29

7-(cyano)-7-deazaguanine + tRNAguanine = guanine + tRNA(7-(cyano)-7-deazaguanine)

644917

1IT8, 3D-view

2.4.2.29

7-(cyano)-7-deazaguanine + tRNAguanine = guanine + tRNA(7-(cyano)-7-deazaguanine)

644917

1P0B, 3D-view

2.4.2.29

7-(cyano)-7-deazaguanine + tRNAguanine = guanine + tRNA(7-(cyano)-7-deazaguanine)

644917

2PWV, 3D-view

2.4.2.29

7-(cyano)-7-deazaguanine + tRNAguanine = guanine + tRNA(7-(cyano)-7-deazaguanine)

644917

2QII, 3D-view

2.4.2.29

pre-queuine 0 + tRNA guanine = guanine + tRNA pre-queuine 0

688390

1IT8, 3D-view

2.4.2.29

pre-queuine 0 + tRNA guanine = guanine + tRNA pre-queuine 0

688390

1P0B, 3D-view

2.4.2.29

pre-queuine 0 + tRNA guanine = guanine + tRNA pre-queuine 0

688390

2PWV, 3D-view

2.4.2.29

pre-queuine 0 + tRNA guanine = guanine + tRNA pre-queuine 0

688390

2QII, 3D-view

2.4.2.48

guanine13 in tRNA(Leu) + 7-cyano-7-carbaguanine = 7-cyano-7-carbaguanine13 in tRNA(Leu) + guanine

745926

-

2.4.2.48

guanine15 in tRNA + 7-cyano-7-carbaguanine = 7-cyano-7-carbaguanine15 in tRNA + guanine

719802, 722604, 728740

-

2.4.2.48

guanine15 in tRNA(Leu) + 7-cyano-7-carbaguanine = 7-cyano-7-carbaguanine15 in tRNA(Leu) + guanine

745926

-

2.4.2.48

guanine15 in tRNA + 7-cyano-7-deazaguanine = 7-cyano-7-deazaguanine15 in tRNA + guanine

738326

-

2.4.2.48

tRNAguanine + 7-cyano-7-deazaguanine = ?

680738

-

1.7.1.13

5 entries

2.4.2.29

8 entries

2.4.2.48

5 entries

Product in Enzyme-catalyzed Reactions (2 results)

top print hide

Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.20

7-carboxy-7-carbaguanine + NH3 + ATP = 7-cyano-7-carbaguanine + ADP + phosphate + H2O

-

-

6.3.4.20

7-carboxy-7-carbaguanine + NH3 + ATP = 7-cyano-7-carbaguanine + AMP + diphosphate + H2O

-

-

6.3.4.20

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.5.1.33

-

712697

-

3D Structure of Enzyme-Ligand-Complex (PDB) (29 results)

top print hide

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (29 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.7.1.13

4FGC, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

1IT8, 3D-view

2.4.2.29

1P0B, 3D-view

2.4.2.29

2PWV, 3D-view

2.4.2.29

2QII, 3D-view

2.4.2.29

28 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

top print hide

Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.7.1.13

0.024

-

pH 7.4, 30°C

743107

1.7.1.13

0.11

-

wild-type, pH 7.5, 25°C

724767

1.7.1.13

0.12

-

pH 7.5, 25°C

742900

1.7.1.13

0.127

-

pH 7.0, 37°C

724879

2.4.2.29

0.0006

-

mutant enzyme E235Q, Km less than 0.0005 mM

688390

2.4.2.29

0.012

-

wild type enzyme

688390

1.7.1.13

4 entries

2.4.2.29

2 entries

K_M Value (6 results)

top print hide

Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.7.1.13

0.00025

-

below 0.25 microM, pH 7.4, 30°C

743107

1.7.1.13

0.001

-

below 1 microM, pH 7.5, 25°C

742900

1.7.1.13

0.0015

-

or below, pH 7.0, 37°C

724879

1.7.1.13

0.0061

-

wild-type, pH 7.5, 25°C

724767

2.4.2.29

0.0005

-

mutant enzyme E235Q, Km less than 0.0005 mM, in 200 mM HEPES, pH 7.3, 20 mM MgCl2

688390

2.4.2.29

0.0009

-

wild type enzyme, in 200 mM HEPES, pH 7.3, 20 mM MgCl2

688390

1.7.1.13

4 entries

2.4.2.29

2 entries

K_i Value (2 results)

top print hide

Show KI Value (2 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.5.1.33

0.0058

-

pH 7.5, temperature not specified in the publication

712697

1.5.1.33

0.027

-

pH 7.5, temperature not specified in the publication, value above 0.027

712697

1.5.1.33

2 entries

References & Links

Literature References (24)

top print hide

Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

644917

372186

Novel mechanism of post-transcriptional modification of tRNA. Insertion of bases of Q precursors into tRNA by a specific tRNA transglycosylase reaction

1979

Okada, N.; Noguchi, S.; Kasai, H.; Shindo-Okada, N.; Ohgi, T.; Goto, T.; Nishimura, S.

J. Biol. Chem.

254

3067-3073

660634

16511203

Crystallization and preliminary x-ray characterization of the nitrile reductase QueF: a queuosine-biosynthesis enzyme

2005

Swairjo, M.A.; Reddy, R.R.; Lee, B.; Van Lanen, S.G.; Brown, S.; de Crecy-Lagard, V.; Iwata-Reuyl, D.; Schimmel, P.

Acta Crystallogr. Sect. F

F61

945-948

662983

353740

Structure determination of a nucleoside Q precursor isolated from E. coli tRNA: 7-(aminomethyl)-7-deazaguanosine

1978

Okada, N.; Noguchi, S.; Nishimura, S.; Ohgi, T.; Goto, T.; Crain, P.F.; McCloskey, J.A.

Nucleic Acids Res.

5

2289-2296

662984

364423

Isolation of Q nucleoside precursor present in tRNA of an E. coli mutant and its characterization as 7-(cyano)-7-deazaguanosine

1978

Noguchi, S.; Yamaizumi, Z.; Ohgi, T.; Goto, T.; Nishimura, Y.; Hirota, Y.; Nishimura, S.

Nucleic Acids Res.

5

4215-4223

663244

15767583

From cyclohydrolase to oxidoreductase: discovery of nitrile reductase activity in a common fold

2005

van Lanen, S.G.; Reader, J.S.; Swairjo, M.A.; de Crecy-Lagard, V.; Lee, B.; Iwata-Reuyl, D.

Proc. Natl. Acad. Sci. USA

102

4264-4269

680738

16407303

The RNA-binding PUA domain of archaeal tRNA-guanine transglycosylase is not required for archaeosine formation

2006

Sabina, J.; Soell, D.

J. Biol. Chem.

281

6993-7001

688390

17949745

Glutamate versus glutamine exchange swaps substrate selectivity in tRNA-guanine transglycosylase: insight into the regulation of substrate selectivity by kinetic and crystallographic studies

2007

Tidten, N.; Stengl, B.; Heine, A.; Garcia, G.A.; Klebe, G.; Reuter, K.

J. Mol. Biol.

374

764-776

712697

19916554

Structure-based design of pteridine reductase inhibitors targeting African sleeping sickness and the leishmaniases

2010

Tulloch, L.B.; Martini, V.P.; Iulek, J.; Huggan, J.K.; Lee, J.H.; Gibson, C.L.; Smith, T.K.; Suckling, C.J.; Hunter, W.N.

J. Med. Chem.

53

221-229

712770

20875425

High-resolution structure of the nitrile reductase QueF combined with molecular simulations provide insight into enzyme mechanism

2010

Kim, Y.; Zhou, M.; Moy, S.; Morales, J.; Cunningham, M.A.; Joachimiak, A.

J. Mol. Biol.

404

127-137

719802

10862614

Hypermodification of tRNA in thermophilic archaea. Cloning, overexpression, and characterization of tRNA-guanine transglycosylase from Methanococcus jannaschii

2000

Bai, Y.; Fox, D.; Lacy, J.; Van Lanen, S.; Iwata-Reuyl, D.

J. Biol. Chem.

275

28731-28738

722604

9242689

Biosynthesis of archaeosine, a novel derivative of 7-deazaguanosine specific to archaeal tRNA, proceeds via a pathway involving base replacement on the tRNA polynucleotide chain

1997

Watanabe, M.; Matsuo, M.; Tanaka, S.; Akimoto, H.; Asahi, S.; Nishimura, S.; Katze, J.R.; Hashizume, T.; Crain, P.F.; McCloskey, J.A.; Okada, N.

J. Biol. Chem.

272

20146-20151

724767

23595998

Targeting the substrate binding site of E. coli nitrile reductase QueF by modeling, substrate and enzyme engineering

2013

Wilding, B.; Winkler, M.; Petschacher, B.; Kratzer, R.; Egger, S.; Steinkellner, G.; Lyskowski, A.; Nidetzky, B.; Gruber, K.; Klempier, N.

Chemistry

19

7007-7012

724879

23410922

Expression and characterization of the nitrile reductase queF from E. coli

2013

Moeller, K.; Nguyen, G.S.; Hollmann, F.; Hanefeld, U.

Enzyme Microb. Technol.

52

129-133

728740

23201278

Purification and comparison of native and recombinant tRNA-guanine transglycosylases from Methanosarcina acetivorans

2013

Nomura, Y.; Onda, Y.; Ohno, S.; Taniguchi, H.; Ando, K.; Oka, N.; Nishikawa, K.; Yokogawa, T.

Protein Expr. Purif.

88

13-19

738326

26663416

Correlation between the stability of tRNA tertiary structure and the catalytic efficiency of a tRNA-modifying enzyme, archaeal tRNA-guanine transglycosylase

2016

Nomura, Y.; Ohno, S.; Nishikawa, K.; Yokogawa, T.

Genes Cells

21

41-52

741484

-

Insight into enzymatic nitrile reduction QM/MM study of the catalytic mechanism of QueF nitrile reductase

2015

Ribeiro, A.; Yang, L.; Ramos, M.; Fernandes, P.; Liang, Z.; Hirao, H.

ACS Catal.

5

3740-3751

742231

-

Substrate and cofactor binding to nitrile reductase A mass spectrometry based study

2016

Gjonaj, L.; Pinkse, M.; Fernandez-Fueyo, E.; Hollmann, F.; Hanefeld, U.

Catal. Sci. Technol.

6

7391-7397

742900

27754868

Kinetic analysis and probing with substrate analogues of the reaction pathway of the nitrile reductase QueF from Escherichia coli

2016

Jung, J.; Czabany, T.; Wilding, B.; Klempier, N.; Nidetzky, B.

J. Biol. Chem.

291

25411-25426

742900

27754868

Kinetic analysis and probing with substrate analogues of the reaction pathway of the nitrile reductase QueF from Escherichia coli

2016

Jung, J.; Czabany, T.; Wilding, B.; Klempier, N.; Nidetzky, B.

J. Biol. Chem.

291

25411-25426

742900

2 entries

743107

-

Biochemical properties of a new nitrile reductase cloned from Pectobacterium carotovorum

2016

Li, M.; Zhou, Z.; Zhang, Z.; Yu, H.; Xu, J.

J. Mol. Catal. B

131

47-54

745926

26721388

Multisite-specific archaeosine tRNA-guanine transglycosylase (ArcTGT) from Thermoplasma acidophilum, a thermo-acidophilic archaeon

2015

Kawamura, T.; Hirata, A.; Ohno, S.; Nomura, Y.; Nagano, T.; Nameki, N.; Yokogawa, T.; Hori, H.

Nucleic Acids Res.

44

1894-1908

745926

26721388

Multisite-specific archaeosine tRNA-guanine transglycosylase (ArcTGT) from Thermoplasma acidophilum, a thermo-acidophilic archaeon

2016

Kawamura, T.; Hirata, A.; Ohno, S.; Nomura, Y.; Nagano, T.; Nameki, N.; Yokogawa, T.; Hori, H.

Nucleic Acids Res.

44

1894-1908

745926

2 entries

764418

-

Interplay of nucleophilic catalysis with proton transfer in the nitrile reductase QueF from Escherichia coli

2019

Jung, J.; Braun, J.; Czabany, T.; Nidetzky, B.

Catal. Sci. Technol.

9

842-853

765048

29339556

Evidence of a sequestered imine intermediate during reduction of nitrile to amine by the nitrile reductase QueF from Escherichia coli

2018

Jung, J.; Nidetzky, B.

J. Biol. Chem.

293

3720-3733

Links to other databases for 7-cyano-7-deazaguanine

top print hide

Show Links (1 entry)