Ligand 5'-deoxyadenosine

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Basic Ligand Information

Molecular Structure
Picture of 5'-deoxyadenosine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H13N5O3
5'-deoxyadenosine
XGYIMTFOTBMPFP-KQYNXXCUSA-N
Synonyms:
5'-deoxy-adenosine

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5'-deoxyadenosine + H2O = 5-deoxy-D-ribose + adenine
show the reaction diagram
5'-deoxyadenosine + H2O = 5-deoxy-D-ribose + adenine
show the reaction diagram
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5'-deoxyadenosine + H2O = 5'-deoxyinosine + NH3
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (49 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehypoxanthine futalosine + S-adenosyl-L-methionine = cyclic dehypoxanthine futalosine + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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magnesium-protoporphyrin IX 13-monomethyl ester + 3 S-adenosyl-L-methionine + H2O = 3,8-divinyl protochlorophyllide a + 3 5'-deoxyadenosine + 3 L-methionine
show the reaction diagram
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a PqqA peptide + S-adenosyl-L-methionine = a PqqA peptide with linked Glu-Tyr residues + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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S-adenosyl-L-methionine + dihydroflavodoxin + [formate C-acetyltransferase]-glycine = 5'-deoxyadenosine + L-methionine + flavodoxin semiquinone + [formate C-acetyltransferase]-glycin-2-yl radical
show the reaction diagram
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2 S-adenosyl-L-methionine + N-acetyldemethylphosphinothricin + reduced acceptor = S-adenosyl-L-homocysteine + 5'-deoxyadenosine + L-methionine + N-acetylphosphinothricin + oxidized acceptor
show the reaction diagram
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2 S-adenosyl-L-methionine + protoheme + 2 reduced flavodoxin = S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + anaerobilin + Fe2+ + 2 oxidized flavodoxin
show the reaction diagram
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5-amino-6-(D-ribitylamino)uracil + L-tyrosine + S-adenosyl-L-methionine = 5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + 2-iminoacetate + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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N6-dimethylallyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-dimethylallyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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N6-L-threonylcarbamoyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
show the reaction diagram
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GTP + S-adenosyl-L-methionine + reduced electron acceptor = (8S)-3',8-cyclo-7,8-dihydroguanosine 5'-triphosphate + 5'-deoxyadenosine + L-methionine + oxidized electron acceptor
show the reaction diagram
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5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + S-adenosyl-L-methionine + reduced acceptor = 5-hydroxybenzimidazole + 5'-deoxyadenosine + L-methionine + formate + NH3 + phosphate + oxidized acceptor
show the reaction diagram
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5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + S-adenosyl-L-methionine = 7,8-didemethyl-8-hydroxy-5-deazariboflavin + NH3 + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5'-deoxyadenosine + H2O = 5-deoxy-D-ribose + adenine
show the reaction diagram
5'-deoxyadenosine + H2O = 6-aminopurine + 5-deoxy-D-ribofuranose
show the reaction diagram
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5'-deoxyadenosine + H2O = 5-deoxy-D-ribose + adenine
show the reaction diagram
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5'-deoxyadenosine + H2O = 5'-deoxyinosine + NH3
show the reaction diagram
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5'-deoxyadenosine + H2O = ?
show the reaction diagram
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5'-deoxyadenosine + H2O = 5'-deoxyinosine + NH3
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (112 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dehypoxanthine futalosine + S-adenosyl-L-methionine = cyclic dehypoxanthine futalosine + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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a PqqA peptide + S-adenosyl-L-methionine = a PqqA peptide with linked Glu-Tyr residues + 5'-deoxyadenosine + L-methionine
show the reaction diagram
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2 S-adenosyl-L-methionine + menaquinone-6 + reduced flavodoxin = S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 8-methylmenaquinone-6 + oxidized flavodoxin
show the reaction diagram
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5-amino-6-(D-ribitylamino)uracil + L-tyrosine + S-adenosyl-L-methionine = 5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + 2-iminoacetate + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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5'-dAMP + thymidine = 5'-deoxyadenosine + TMP
show the reaction diagram
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N6-L-threonylcarbamoyladenine37 in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N6-L-threonylcarbamoyladenine37 in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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N1-methylguanine37 in tRNAPhe + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine37 in tRNAPhe + L-methionine + 5'-deoxyadenosine + CO2 + H2O
show the reaction diagram
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L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H+
show the reaction diagram
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5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + S-adenosyl-L-methionine + reduced acceptor = 5-hydroxybenzimidazole + 5'-deoxyadenosine + L-methionine + formate + NH3 + phosphate + oxidized acceptor
show the reaction diagram
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5-amino-5-(4-hydroxybenzyl)-6-(D-ribitylimino)-5,6-dihydrouracil + S-adenosyl-L-methionine = 7,8-didemethyl-8-hydroxy-5-deazariboflavin + NH3 + L-methionine + 5'-deoxyadenosine
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
and analogues; strong, competitive
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cooperative inhibition by with Met

3D Structure of Enzyme-Ligand-Complex (PDB) (35 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.8
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-
0.078
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at pH 7.0 and 35°C
0.017
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wild type enzyme, at pH 7.5 and at 30°C

KM Value (11 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.65
-
-
0.042
-
wild type enzyme, at pH 7.5 and at 30°C

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.01
-
pH 7.5, 25°C
0.012
-
pH 8.0, 37°C, recombinant His-tagged enzyme

References & Links

Links to other databases for 5'-deoxyadenosine

ChEBI
PubChem
ChEBI
PubChem