Page last updated: 2024-10-24
2'-deoxyadenosine deaminase activity
Definition
Target type: molecularfunction
Catalysis of the reaction: 2'-deoxyadenosine + H2O = deoxyinosine + NH3. [GOC:ai, RHEA:28190]
2'-deoxyadenosine deaminase (dADA) activity catalyzes the hydrolytic deamination of 2'-deoxyadenosine to 2'-deoxyinosine. This reaction is essential for the purine salvage pathway, which recycles purine bases from degraded nucleic acids to form new nucleotides. The enzyme utilizes a zinc ion as a cofactor to facilitate the deamination process. The catalytic mechanism involves the abstraction of a proton from the N3 position of 2'-deoxyadenosine, followed by nucleophilic attack by a water molecule on the C6 atom. The resulting intermediate is then hydrolyzed to produce 2'-deoxyinosine and ammonia. dADA activity is crucial for maintaining cellular nucleotide pools and preventing the accumulation of 2'-deoxyadenosine, which can inhibit DNA synthesis and cell proliferation. Mutations in the dADA gene can lead to severe combined immunodeficiency (SCID), a life-threatening condition characterized by impaired immune function.'
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Proteins (2)
| Protein | Definition | Taxonomy |
|---|---|---|
| Adenosine deaminase | An adenosine deaminase that is encoded in the genome of cow. [OMA:P56658, PRO:DNx] | Bos taurus (cattle) |
| Adenosine deaminase | An adenosine deaminase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P00813] | Homo sapiens (human) |
Compounds (30)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| 9-(2-hydroxy-3-nonyl)adenine | 9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase | ||
| benzil | benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively. benzil: structure | alpha-diketone; aromatic ketone | |
| 2-chloroadenosine | 5-chloroformycin A: structure given in first source | purine nucleoside | |
| 2-fluoroadenosine | adenosines; organofluorine compound | ||
| 2'-deoxyadenosine | 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source | purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside | Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite |
| dideoxyadenosine | Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite. | adenosines; purine 2',3'-dideoxyribonucleoside | EC 3.5.4.4 (adenosine deaminase) inhibitor; EC 4.6.1.1 (adenylate cyclase) inhibitor |
| vidarabine | adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond. | beta-D-arabinoside; purine nucleoside | antineoplastic agent; bacterial metabolite; nucleoside antibiotic |
| 3-deazaadenosine | 3-deazaadenosine: RN given refers to parent cpd. | ||
| coformycin | coformycins | EC 3.5.4.4 (adenosine deaminase) inhibitor | |
| adefovir | adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection. adefovir: inhibitor of African swine fever virus adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). | 6-aminopurines; ether; phosphonic acids | antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent |
| adenosine | quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit | adenosines; purines D-ribonucleoside | analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent |
| 2'3'-didehydro-2'3'-dideoxyadenosine | 2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source | ||
| nebularine | nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage. nebularine: structure | purine ribonucleoside; purines D-ribonucleoside | fungal metabolite |
| 2-aminoadenosine | purine nucleoside | ||
| 2,6-diamino-9-(2-hydroxyethoxymethyl)purine | 2,6-diamino-9-(2-hydroxyethoxymethyl)purine: adenosine deaminase converts above cpd to acylovir | ||
| 8-azaadenosine | N-glycosyl compound | ||
| 8-aminoadenosine | |||
| 6-methoxypurine arabinoside | |||
| 9-(2-hydroxy-3-nonyl)adenine | (2R,3S)-EHNA : EHNA of absolute configuration 2R,3S. Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase. | EHNA | EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor |
| 9-(2-hydroxy-3-nonyl)adenine | (2S,3R)-EHNA : EHNA of absolute configuration 2S,3R. | EHNA | |
| 1-deazaadenosine | 1-deazaadenosine: inhibits nucleic acid & protein synthesis; structure given in first source | ||
| pentostatin | pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia. Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity. | coformycins | antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor |
| formycin | formycin | antineoplastic agent | |
| 1-deaza-2-chloro-n(6)-cyclopentyladenosine | 1-deaza-2-chloro-N(6)-cyclopentyladenosine: adenosine A(1) receptor agonist | ||
| fludarabine | purine nucleoside | ||
| 8-azanebularine | 8-azanebularine: structure in first source | ||
| msh, 4-nle-7-phe-alpha- | polypeptide | dermatologic drug | |
| deoxyinosine | purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside | Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite | |
| inosine | inosines; purines D-ribonucleoside | Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite | |
| adenallene | adenallene: structure given in first source; inhibits replication and cytopathic effects of HIV in vitro |