Target type: biologicalprocess
The chemical reactions and pathways involving adenine, 6-aminopurine, one of the five main bases found in nucleic acids and a component of numerous important derivatives of its corresponding ribonucleoside, adenosine. [GOC:go_curators]
Adenine metabolism is a complex process that involves the synthesis, degradation, and utilization of adenine, a purine base that is an essential component of DNA, RNA, and ATP.
**Synthesis:**
Adenine is synthesized de novo from simpler molecules, primarily through the purine biosynthesis pathway. This pathway involves a series of enzymatic steps that begin with the amino acids glycine, glutamine, aspartate, and formate. The key intermediates in this pathway include inosine monophosphate (IMP), adenosine monophosphate (AMP), and guanosine monophosphate (GMP).
**Degradation:**
Adenine can be degraded through a series of enzymatic reactions that ultimately produce uric acid, the primary end product of purine metabolism in humans. The process begins with the deamination of adenine to hypoxanthine by the enzyme adenine deaminase. Hypoxanthine is then oxidized to xanthine by xanthine oxidase. Finally, xanthine is oxidized to uric acid by the same enzyme.
**Utilization:**
Adenine is utilized in a variety of cellular processes, including:
* **DNA and RNA synthesis:** Adenine is a component of both DNA and RNA, and its synthesis and degradation are essential for the replication and transcription of genetic information.
* **ATP synthesis:** Adenine is a component of ATP, the primary energy currency of cells. ATP is generated through the process of oxidative phosphorylation, which involves the transfer of electrons from reduced coenzymes (NADH and FADH2) to molecular oxygen, coupled to the phosphorylation of ADP to ATP.
* **Signal transduction:** Adenine derivatives, such as cyclic AMP (cAMP), play important roles in signal transduction pathways. cAMP is a second messenger that mediates the effects of hormones and other signaling molecules.
**Regulation:**
The synthesis and degradation of adenine are tightly regulated to maintain cellular homeostasis. This regulation is achieved through a variety of mechanisms, including feedback inhibition, allosteric regulation, and transcriptional control.
**Disorders of Adenine Metabolism:**
Defects in the genes that encode enzymes involved in adenine metabolism can lead to a variety of disorders, including:
* **Lesch-Nyhan syndrome:** This rare genetic disorder is caused by a deficiency in the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRT). This deficiency results in a build-up of uric acid in the body, leading to a variety of symptoms, including self-injurious behavior, mental retardation, and gout.
* **Adenine phosphoribosyltransferase deficiency:** This disorder is characterized by an accumulation of adenine in the body, which can lead to a variety of neurological and developmental problems.
Adenine metabolism is a fundamental process that is essential for life. Defects in this process can lead to serious health problems, highlighting the importance of understanding the regulation and function of adenine metabolic pathways.'
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Protein | Definition | Taxonomy |
---|---|---|
Hypoxanthine-guanine phosphoribosyltransferase | A hypoxanthine-guanine phosphoribosyltransferase that is encoded in the genome of human. [PRO:DNx, UniProtKB:P00492] | Homo sapiens (human) |
Compound | Definition | Classes | Roles |
---|---|---|---|
chrysene | chrysene : An ortho-fused polycyclic arene found commonly in the coal tar. chrysene: structure in Merck Index, 9th ed, #2252 | ortho-fused polycyclic arene | plant metabolite |
6-chrysenamine | 6-chrysenamine: may cause splenic atrophy and leukopenia; minor descriptor (76-84); on-line & Index Medicus search PHENANTHRENES (76-84) | carbopolycyclic compound | |
6-nitrochrysene | 6-nitrochrysene: RN given refers to cpd with locant for nitro group in position 6 | carbopolycyclic compound | |
mercaptopurine | mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis. Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. purine-6-thiol : A thiol that is the tautomer of mercaptopurine. | aryl thiol; purines; thiocarbonyl compound | anticoronaviral agent; antimetabolite; antineoplastic agent |
thioguanine anhydrous | Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia. | 2-aminopurines | anticoronaviral agent; antimetabolite; antineoplastic agent |
guanosine monophosphate | guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase. Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature. | guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate | biomarker; Escherichia coli metabolite; metabolite; mouse metabolite |
guanine | 2-aminopurines; oxopurine; purine nucleobase | algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite | |
hypoxanthine | nucleobase analogue; oxopurine; purine nucleobase | fundamental metabolite | |
inosinic acid | Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety. | inosine phosphate; purine ribonucleoside 5'-monophosphate | Escherichia coli metabolite; human metabolite; mouse metabolite |
allopurinol | allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring. Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms. | nucleobase analogue; organic heterobicyclic compound | antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger |
azaguanine | 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively. Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids. | nucleobase analogue; triazolopyrimidines | antimetabolite; antineoplastic agent; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor |