adenine, organic base of the purine family. Adenine combines with the sugar ribose to form adenosine, which in turn can be bonded with from one to three phosphoric acid units, yielding the three nucleotides adenosine monophosphate, adenosine diphosphate, and adenosine triphosphate. These adenine derivatives perform important functions in cellular metabolism. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. A modified form of adenosine monophosphate is thought to be a secondary messenger in the propagation of many hormonal stimuli. Adenine is an integral part of the structure of many coenzymes.

Organic compound of the purine family, often called a base, consisting of two rings, each containing both nitrogen and carbon atoms, and an amino group. It occurs free in tea and in combined form in nucleic acids, ATP, vitamin B₁₂, and several coenzymes. In DNA its complementary base is thymine. It or its corresponding nucleoside or nucleotide may be prepared from nucleic acids by selective techniques of hydrolysis.

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Adenine is a purine with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), and protein synthesis, as a chemical component of DNA and RNA. the shape of adenine is complementary to either thymine or uracil.

Structure

It forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent.

Biosynthesis

The Purine metabolism involves the formation of Adenine and Guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which is synthesised on a pre-existing ribose through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as formate ions transferred from the coenzyme tetrahydrofolate.

Function

Adenine is one of the two purine nucleobases (the other being guanine) used in forming nucleotides of the nucleic acids. In DNA, adenine binds to thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. In RNA, which is used in the cytoplasm for protein synthesis, adenine binds to uracil.

Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose. It forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions.

History

In older literature, adenine was sometimes called Vitamin B4. It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), respectively.

Some think that, at the origin of life on Earth, the first adenine was formed by the polymerization of five hydrogen cyanide (HCN) molecules. However, this has been criticized by some chemists.

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