Description
adenine is one of the purine nitrogenous bases that composes DNA and RNA; composed of two carbon–nitrogen rings. Adenine bonds with thymine in DNA and with uracil in RNA (see base pairing rule); it is also a major component of other molecules such as adenosine triphosphate.
Chemical Properties
Adenine is a prominent member of the family of naturally occurring purines. Adenine occurs not only in ribonucleic acids (RNA), and deoxyribonucleic acids (DNA), but in nucleosides, such as adenosine, and nucleotides, such as adenylic acid, which may be linked with enzymatic functions quite apart from nucleic acids. Adenine, in the form of its ribonucleotide, is produced in mammals and fowls endogenously from smaller molecules and no nutritional essentiality is ascribed to it. In the nucleosides, nucleotides, and nucleic acids, the attachment or the sugar moiety is at position 9.
The purines and pyrimidines absorb ultraviolet light readily, with absorption peaks at characteristic frequencies. This has aided in their identification and quantitative determination.
Physical properties
Adenine is a white to almost white crystalline powder that is an important biological compound found in deoxyribonucleic acid (DNA), ribonucleic acid (RNA), and adenosine triphosphate (ATP). It was once commonly referred to as vitamin B4 but is no longer considered a vitamin. Adenine is derived from purine. Purine is a heterocyclic compound.
History
Adenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.
Uses
Adenine is used as an active component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron. It is useful as a local antiseptic and vitamin B4. Further, it is used in the microbial determination of niacin. It is also employed as a food supplement for adult rats to investigate the effects of dietary adenine overload. In addition to this, it is used in the production of nucleotides of the nucleic acids.
Definition
ChEBI: Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine.
Application
Widespread throughout animal and plant tissues combined with niacinamide, d-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coa laninedehydrase. It is used in microbial determination of niacin; in research on heredity, virus diseases, and cancer.
Synthesis Reference(s)
Journal of the American Chemical Society, 88, p. 3829, 1966
DOI: 10.1021/ja00968a028
General Description
Adenine is a purine nucleobase. It is part of DNA, and RNA. Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP). It is a nitrogenous base found in DNA and RNA. It is also a constituent of certain coenzymes and when combined with the sugar ribose it forms the nucleoside adenosine found in AMP, ADP, and ATP. Adenine has a purine ring structure. It is one of the major component bases ofnucleotides and the nucleic acidsDNA and RNA.
Biochem/physiol Actions
Adenine is essential for many in vivo and in vitro biochemical processes. Adenine is converted to adenosine with ribose. On phosphorylation, it forms AMP, ADP and ATP. ATP is the energy currency of the cell and is required during cellular metabolism. Adenine is metabolized to is 2,8-dihydroxyadenine, which on accumulation in proximal tubules leads to the induction of chronic kidney disease (CKD) with severe anemia in rats. Adenine based derivatives elicit antiviral functionality against dsDNA viruses and are exploited for generating antiviral scaffolds.
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.
Synthesis
A novel method for synthesizing adenine, comprising the steps of:
(1) firstly dispersing acetyl hypoxanthine in 1,2- dichloroethane, and then adding it to the reactor, slowly putting in anhydrous pyridine and triethylamine, stirring to raise the temperature to 110 -120 , adding phosphorus triclosan to keep warm and reacting for 50-80 minutes, and then continuing to keep warm and reacting at 110 -120 for 4-6 hours and then lowering the temperature to 15 or so, and static till overnight;
(2) The above reaction solution was filtered, and then added into ammonia/methanol mixture for ammonolysis, and then dried to get the crude adenine product;
(3) the crude adenine into the reactor, feeding the end of the temperature to 80 to make it clear, to be adenine all dissolved to join the activated carbon for decolorization, continue to 80 insulation decolorization for 2 hours, filtration and separation of activated carbon;
(4) After filtration, ammonia, crystallization, filtration, washing with a small amount of distilled water, drying, that is, adenine pure product.
Purification Methods
Crystallise adenine from distilled water. [Beilstein 26 III/IV 3561.]
