HOME

TheInfoList




Adenine (A, Ade) is a
nucleobase 230px, Pyrimidine nucleobases are simple ring molecules. Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides Nucleosides are glycosylamines that can be ...
(a
purine Purine is a heterocyclic 125px, Pyridine, a heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different chemical element, elements as members of its ring(s). Heterocyclic chemi ...

purine
derivative). It is one of the four nucleobases in the
nucleic acid Nucleic acids are biopolymers, macromolecules, essential to all Organism, known forms of life. They are composed of nucleotides, which are the monomers made of three components: a pentose, 5-carbon sugar, a phosphate group and a nitrogenous base. ...

nucleic acid
of
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
that are represented by the letters G–C–A–T. The three others are
guanine Guanine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

guanine
,
cytosine Cytosine () (symbol A symbol is a mark, sign, or that indicates, signifies, or is understood as representing an , , or . Symbols allow people to go beyond what is n or seen by creating linkages between otherwise very different s and s. Al ...

cytosine
and
thymine Thymine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

thymine
. Its derivatives have a variety of roles in
biochemistry Biochemistry or biological chemistry, is the study of es within and relating to living s. A sub-discipline of both and , biochemistry may be divided into three fields: , and . Over the last decades of the 20th century, biochemistry has beco ...

biochemistry
including
cellular respiration upright=2.5, Typical eukaryotic cell Cellular respiration is a set of metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life Life is a characteristic that distinguishes physical entities ...

cellular respiration
, in the form of both the energy-rich
adenosine triphosphate Adenosine triphosphate (ATP) is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properti ...

adenosine triphosphate
(ATP) and the cofactors
nicotinamide adenine dinucleotide Nicotinamide adenine dinucleotide (NAD) is a coenzyme A cofactor is a non-protein Proteins are large biomolecules or macromolecules that are comprised of one or more long chains of amino acid residue (biochemistry), residues. Proteins pe ...
(NAD),
flavin adenine dinucleotide In biochemistry Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biolo ...

flavin adenine dinucleotide
(FAD) and
Coenzyme A Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the Fatty acid metabolism#Synthesis, synthesis and Fatty acid metabolism#.CE.B2-Oxidation, oxidation of fatty acids, and the oxidation of pyruvic acid, pyruvate in the citric aci ...
. It also has functions in
protein synthesis Protein biosynthesis (or protein synthesis) is a core biological process, occurring inside cells Cell most often refers to: * Cell (biology), the functional basic unit of life Cell may also refer to: Closed spaces * Monastic cell, a small roo ...
and as a chemical component of
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
and
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
. The shape of adenine is complementary to either
thymine Thymine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

thymine
in
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
or
uracil Uracil () ( U or Ura) is one of the four s in the that are represented by the letters A, G, C and U. The others are (A), (C), and (G). In RNA, uracil binds to via two . In , the uracil nucleobase is replaced by . Uracil is a form of . Ura ...

uracil
in
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
. The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a
covalent bond A covalent bond is a chemical bond A chemical bond is a lasting attraction between atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes ...
is formed between
deoxyribose Deoxyribose, or more precisely 2-deoxyribose, is a monosaccharide Monosaccharides (from Greek '' monos'': single, ''sacchar'': sugar), also called simple sugars, are the simplest form of sugar Sugar is the generic name for Sweetness, sweet ...

deoxyribose
sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an ''adenine residue'', as part of a larger molecule.
Adenosine Adenosine is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, cate ...

Adenosine
is adenine reacted with
ribose Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this compoun ...

ribose
, as used in
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
and ATP; deoxyadenosine is adenine attached to
deoxyribose Deoxyribose, or more precisely 2-deoxyribose, is a monosaccharide Monosaccharides (from Greek '' monos'': single, ''sacchar'': sugar), also called simple sugars, are the simplest form of sugar Sugar is the generic name for Sweetness, sweet ...

deoxyribose
, as used to form DNA.


Structure

Adenine forms several
tautomer Tautomers () are structural isomer In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, ...

tautomer
s, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.


Biosynthesis

Purine metabolism Purine metabolism refers to the metabolic pathways to synthesize and break down purine Purine is a heterocyclic compound, heterocyclic aromatic organic compound that consists of two rings (pyrimidine and imidazole). It is water-soluble. Purine a ...
involves the formation of adenine and
guanine Guanine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

guanine
. Both adenine and guanine are derived from the nucleotide
inosine monophosphate Inosinic acid or inosine monophosphate (IMP) is a nucleotide Nucleotides are organic molecules consisting of a nucleoside and a phosphate. They serve as monomeric units of the nucleic acid polymers deoxyribonucleic acid (DNA) and ribonucleic a ...

inosine monophosphate
(IMP), which in turn is synthesized from a pre-existing
ribose phosphate Ribose 5-phosphate (R5P) is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose 5-phosphate. Depending on the body's state, r ...
through a complex pathway using atoms from the amino acids
glycine Glycine (symbol Gly or G; ) is an amino acid Amino acids are organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond ...

glycine
,
glutamine Glutamine (symbol Gln or Q) is an α-amino acid Amino acids are organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bo ...

glutamine
, and aspartic acid, as well as the coenzyme
tetrahydrofolate
tetrahydrofolate
.


Manufacturing Method

Patented Aug. 20, 1968, the current recognized method of industrial-scale production of adenine is a modified form of the formamide method. This method heats up formamide under 120 degree celcius conditions within a sealed flask for 5 hours to form adenine. The reaction is heavily increased  in quantity by using a phosphorus oxychloride (phosphoryl chloride) or phosphorus pentachloride as an acid catalyst and sunlight or ultraviolet conditions. After the 5 hours have passed and the formamide-phosphorus oxychloride-adenine solution cools down, water is put into the flask containing the formamide and now-formed adenine. The water-formamide-adenine solution is then poured through a filtering column of activated charcoal. The water and formamide molecules, being small molecules, will pass through the charcoal and into the waste flask; the large adenine molecules, however, will attach or “adsorb” to the charcoal due to the van der waals forces that interact between the adenine and the carbon in the charcoal. Because charcoal has a large surface area, it's able to capture the majority of molecules that pass a certain size (greater than water and formamide) through it. To extract the adenine from the charcoal-adsorbed adenine, ammonia gas dissolved in water ( aqua ammonia) is poured onto the activated charcoal-adenine structure to liberate the adenine into the ammonia-water solution. The solution containing water, ammonia, and adenine is then left to air dry, with the adenine losing solubility due to the loss of ammonia gas that previously made the solution basic and capable of dissolving adenine, thus causing it to crystalize into a pure white powder that can be stored.


Function

Adenine is one of the two purine
nucleobase 230px, Pyrimidine nucleobases are simple ring molecules. Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides Nucleosides are glycosylamines that can be ...
s (the other being
guanine Guanine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

guanine
) used in forming
nucleotide Nucleotides are organic molecules , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...

nucleotide
s of the
nucleic acid Nucleic acids are biopolymers, macromolecules, essential to all Organism, known forms of life. They are composed of nucleotides, which are the monomers made of three components: a pentose, 5-carbon sugar, a phosphate group and a nitrogenous base. ...

nucleic acid
s. In DNA, adenine binds to
thymine Thymine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

thymine
via two
hydrogen bond A hydrogen bond (or H-bond) is a primarily Electrostatics, electrostatic force of attraction between a hydrogen Hydrogen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of ...

hydrogen bond
s to assist in stabilizing the nucleic acid structures. In RNA, which is used for
protein synthesis Protein biosynthesis (or protein synthesis) is a core biological process, occurring inside cells Cell most often refers to: * Cell (biology), the functional basic unit of life Cell may also refer to: Closed spaces * Monastic cell, a small roo ...
, adenine binds to
uracil Uracil () ( U or Ura) is one of the four s in the that are represented by the letters A, G, C and U. The others are (A), (C), and (G). In RNA, uracil binds to via two . In , the uracil nucleobase is replaced by . Uracil is a form of . Ura ...

uracil
. Adenine forms
adenosine Adenosine is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, cate ...

adenosine
, a
nucleoside Nucleosides are s that can be thought of as s without a . A nucleoside consists simply of a (also termed a nitrogenous base) and a five-carbon sugar ( or 2'-deoxyribose) whereas a nucleotide is composed of a nucleobase, a five-carbon sugar, and ...

nucleoside
, when attached to
ribose Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this compoun ...

ribose
, and
deoxyadenosine Deoxyadenosine (symbol dA or dAdo) is a deoxyribonucleoside A deoxyribonucleoside is a type of nucleoside including deoxyribose as a component. An example is deoxycytidine. References {{organic-compound-stub Nucleosides, * .... It is a deriva ...
when attached to
deoxyribose Deoxyribose, or more precisely 2-deoxyribose, is a monosaccharide Monosaccharides (from Greek '' monos'': single, ''sacchar'': sugar), also called simple sugars, are the simplest form of sugar Sugar is the generic name for Sweetness, sweet ...

deoxyribose
. It forms
adenosine triphosphate Adenosine triphosphate (ATP) is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properti ...

adenosine triphosphate
(ATP), a
nucleoside triphosphate Nucleosides are glycosylamine 120px, Cyclic hemiaminal ether bond derived from an aldehyde Glycosylamines are a class of biochemical compounds consisting of a Glycosyl, glycosyl group attached to an amine, amino group, -NR2. They are also known ...
, when three
phosphate group In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of atoms ...

phosphate group
s are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring
chemical energy Chemical energy is the energy of chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects th ...
between
chemical reactions A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical A chemical substance is a form of matter having constant chemical composition and characteristic ...

chemical reactions
. :


History

In older literature, adenine was sometimes called Vitamin B4. Due to it being synthesized by the body and not essential to be obtained by diet, it does not meet the definition of
vitamin A vitamin is an organic molecule , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, ...
and is no longer part of the
Vitamin B B vitamins are a class of water-soluble vitamin A vitamin is an organic molecule , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond ...
complex. However, two B vitamins,
niacin Niacin, also known as nicotinic acid, is an organic compound and a form of vitamin B3, vitamin B3, an essential nutrient, essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtaine ...

niacin
and
riboflavin Riboflavin, also known as vitamin B2, is a vitamin found in food and used as a dietary supplement. It is required by the body for cellular respiration. Food sources include egg (food), eggs, green vegetables, milk and other dairy products, meat, ...

riboflavin
, bind with adenine to form the essential cofactors
nicotinamide adenine dinucleotide Nicotinamide adenine dinucleotide (NAD) is a coenzyme A cofactor is a non-protein Proteins are large biomolecules or macromolecules that are comprised of one or more long chains of amino acid residue (biochemistry), residues. Proteins pe ...
(NAD) and
flavin adenine dinucleotide In biochemistry Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biolo ...

flavin adenine dinucleotide
(FAD), respectively.
Hermann Emil Fischer Hermann Emil Louis Fischer FRS FRSE FCS (c; ; 9 October 185215 July 1919) was a German chemist and 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He also developed the Fischer projection, a symbol ...

Hermann Emil Fischer
was one of the early scientists to study adenine. It was named in 1885 by
Albrecht Kossel Ludwig Karl Martin Leonhard Albrecht Kossel (; 16 September 1853 – 5 July 1927) was a German and pioneer in the study of . He was awarded the Nobel Prize for in 1910 for his work in determining the chemical composition of s, the genetic subst ...
, in reference to the pancreas (a specific
gland In animals, a gland is a group of cells in an animal's body that synthesizes substances (such as hormone A hormone (from the Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), offic ...

gland
- in
Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is approximately 10.7 million as of ...
, ''ἀδήν'' "aden") from which Kossel's sample had been extracted. Experiments performed in 1961 by
Joan Oró
Joan Oró
have shown that a large quantity of adenine can be synthesized from the
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks.Clayden, J ...
of
ammonia Ammonia is a compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fort ...

ammonia
with five
hydrogen cyanide
hydrogen cyanide
(HCN) molecules in aqueous solution; whether this has implications for the
origin of life In evolutionary biology, abiogenesis, or informally the origin of life (OoL),Compare: is the natural process by which life has arisen from non-living matter, such as simple organic compounds. While the details of this process are still unkn ...
on
Earth Earth is the third planet from the Sun and the only astronomical object known to harbour and support life. 29.2% of Earth's surface is land consisting of continents and islands. The remaining 70.8% is Water distribution on Earth, covered wi ...

Earth
is under debate. On August 8, 2011, a report, based on
NASA The National Aeronautics and Space Administration (NASA; ) is an independent agencies of the United States government, independent agency of the Federal government of the United States, U.S. federal government responsible for the civilian Li ...

NASA
studies with
meteorites A meteorite is a solid piece of debris from an object, such as a comet A comet is an icy, small Solar System body A small Solar System body (SSSB) is an object in the Solar System The Solar SystemCapitalization of the name varies ...

meteorites
found on
Earth Earth is the third planet from the Sun and the only astronomical object known to harbour and support life. 29.2% of Earth's surface is land consisting of continents and islands. The remaining 70.8% is Water distribution on Earth, covered wi ...

Earth
, was published suggesting building blocks of
DNA Deoxyribonucleic acid (; DNA) is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrically neutral gro ...

DNA
and
RNA Ribonucleic acid (RNA) is a polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Re ...

RNA
(adenine,
guanine Guanine () (symbol A symbol is a mark, sign, or word In linguistics, a word of a spoken language can be defined as the smallest sequence of phonemes that can be uttered in isolation with semantic, objective or pragmatics, practical meaning ...

guanine
and related
organic molecules , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, catenate (form chains with other carbon ...
) may have been formed extraterrestrially in
outer space Outer space, commonly shortened to space, is the expanse that exists beyond Earth Earth is the third planet from the Sun and the only astronomical object known to harbour and support life. 29.2% of Earth's surface is land consisting ...
. In 2011, physicists reported that adenine has an "unexpectedly variable range of ionization energies along its reaction pathways" which suggested that "understanding experimental data on how adenine survives exposure to
UV light Ultraviolet (UV) is a form of with from 10 (with a corresponding frequency around 30 ) to 400 nm (750 ), shorter than that of , but longer than s. UV radiation is present in , and constitutes about 10% of the total electromagnetic radi ...
is much more complicated than previously thought"; these findings have implications for
spectroscopic Spectroscopy is the study of the interaction between matter and Electromagnetism, electromagnetic radiation as a function of the wavelength or frequency of the radiation. In simpler terms, spectroscopy is the precise study of color as generalize ...

spectroscopic
measurements of
heterocyclic 125px, Pyridine, a heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different chemical element, elements as members of its ring(s). Heterocyclic chemistry is the branch of organi ...
compounds, according to one report.


References


External links


Vitamin B4 MS Spectrum
{{Authority control Nucleobases Purines Vitamins