Adenine

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.

Chemical Properties

White to almost white crystalline powder

Physical properties

Adenine is a white crystalline substance 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

A purine nucleobase and a component of DNA

Uses

enteric coating

Uses

local antiseptic

Uses

Vitamin B4

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.

Uses

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.

Definition

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.

Definition

adenine: A purine derivative. It isone of the major component bases ofnucleotides and the nucleic acidsDNA and RNA.

Definition

ChEBI: The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6.

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 3829, 1966 DOI: 10.1021/ja00968a028

General Description

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,.

Purification Methods

Crystallise adenine from distilled water. [Beilstein 26 III/IV 3561.]