Target type: biologicalprocess
The chemical reactions and pathways involving a nucleotide, a nucleoside that is esterified with (ortho)phosphate or an oligophosphate at any hydroxyl group on the glycose moiety; may be mono-, di- or triphosphate; this definition includes cyclic nucleotides (nucleoside cyclic phosphates). [GOC:ma]
Nucleotide metabolism is a fundamental biological process that encompasses the synthesis, degradation, and interconversion of nucleotides, the building blocks of DNA and RNA. It is an essential process for life, playing vital roles in genetic information storage and transmission, energy production, and cellular signaling.
**Nucleotide Synthesis:**
* **De novo synthesis:** This pathway starts with simple precursors like amino acids, ribose-5-phosphate, and CO2. These precursors are converted into purine and pyrimidine bases, which are then attached to ribose-5-phosphate to form nucleotides.
* **Salvage pathway:** This pathway recycles pre-existing purine and pyrimidine bases from degraded nucleic acids. These bases are then converted into nucleotides.
**Nucleotide Degradation:**
* **Purine degradation:** Purine nucleotides are broken down into uric acid, which is excreted in the urine.
* **Pyrimidine degradation:** Pyrimidine nucleotides are broken down into β-alanine and β-aminoisobutyrate, which are further metabolized.
**Interconversion of Nucleotides:**
* **Ribonucleotide reductase:** This enzyme converts ribonucleotides (with a ribose sugar) to deoxyribonucleotides (with a deoxyribose sugar), which are used in DNA synthesis.
* **Phosphorylation and dephosphorylation:** Nucleotides can be interconverted by adding or removing phosphate groups, affecting their energy content and activity.
**Regulation of Nucleotide Metabolism:**
* **Feedback inhibition:** The end products of nucleotide synthesis can inhibit the enzymes involved in the early steps of their own synthesis.
* **Hormonal control:** Hormones like insulin and glucagon can influence nucleotide metabolism.
* **Genetic factors:** Mutations in genes involved in nucleotide metabolism can lead to genetic disorders.
**Biological Importance:**
* **DNA replication and repair:** Nucleotides are essential for DNA synthesis and repair, ensuring the integrity of genetic information.
* **RNA transcription and translation:** RNA is synthesized using nucleotides, and plays a crucial role in protein synthesis.
* **Energy metabolism:** Nucleotides like ATP and GTP are involved in energy transfer and cellular processes.
* **Cellular signaling:** Nucleotides act as signaling molecules, involved in cell communication and regulation.
**Disorders of Nucleotide Metabolism:**
* **Lesch-Nyhan syndrome:** A rare genetic disorder caused by a deficiency in the enzyme hypoxanthine-guanine phosphoribosyltransferase, leading to uric acid accumulation.
* **Severe combined immunodeficiency (SCID):** Certain types of SCID are caused by defects in enzymes involved in nucleotide metabolism, affecting immune function.
* **Cancer:** Dysregulation of nucleotide metabolism can contribute to cancer development and progression.
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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-like protein | An adenosine deaminase-like protein that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q6DHV7] | Homo sapiens (human) |
Compound | Definition | Classes | Roles |
---|---|---|---|
adenosine monophosphate | Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. | adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate | adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical |
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 | |||
o(6)-methyldeoxyguanylic acid | O(6)-methyldeoxyguanylic acid: incorporated into DNA by DNA polymerase I & II | ||
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 | ||
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 |