Adenine: Difference between revisions

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('''A''', '''Ade''') is a [[nucleobase]] associated with [[biochemistry]]. As a [[purine]] derivative, it has several essential roles in biological processes. This article explores the structure, synthesis, function, and history of adenine.
{{SI}}
[[File:Adenine numbered.svg|thumb|left|150px|Numbered structure of adenine.]]
 
'''Adenine''' ('''A''', '''Ade''') is a [[nucleobase]] classified as a [[purine]] derivative, and plays a critical role in numerous [[biochemical]] processes. It is a key component of both [[DNA]] and [[RNA]], as well as several essential cofactors and cellular energy molecules.
 
== Overview ==
Adenine is fundamental in [[cellular respiration]], forming part of [[adenosine triphosphate]] ('''ATP'''), the principal molecule for storing and transferring [[chemical energy]] in [[cells]]. It is also present in the important [[cofactor]]s [[nicotinamide adenine dinucleotide]] ('''NAD''') and [[flavin adenine dinucleotide]] ('''FAD''').


==Overview==
In the context of [[genetic material]], adenine is one of the four nucleobases in [[DNA]], where it forms [[base pair]]s with [[thymine]] through [[hydrogen bond]]s. In [[RNA]], adenine pairs with [[uracil]] during [[transcription]] and [[protein biosynthesis]].
Adenine is an integral part of [[cellular respiration]], specifically in the formation of the energy-rich molecule [[adenosine triphosphate]] (ATP). Moreover, it acts as a constituent of the [[cofactor (biochemistry)|cofactor]]s [[nicotinamide adenine dinucleotide]] (NAD) and flavin adenine dinucleotide ([[FAD]]). Furthermore, it is pivotal in [[Protein biosynthesis|protein synthesis]], being a primary component of both [[DNA]] and [[RNA]]. In DNA, adenine pairs with [[thymine]], whereas in RNA, it complements [[uracil]].<ref>[http://ghr.nlm.nih.gov/ghr/glossary/adenine Genetics Home Reference] - [[National Institutes of Health]]</ref>


==Structure==
== Structure ==
[[File:Adenine numbered.svg|thumb|left|150px|Numbered structure of adenine.]]
Adenine is a heterocyclic compound composed of a fused [[imidazole]] and [[pyrimidine]] ring—together forming the purine structure. It exists in several [[tautomer]]ic forms, which interconvert rapidly in aqueous solutions. The predominant tautomer under isolated conditions (e.g., in the gas phase or inert matrices) is the 9H-adenine.
Several [[tautomer]]s of adenine exist, which can rapidly interconvert, leading them often to be treated as equivalent. Notably, under specific isolated conditions, such as in an inert gas matrix or in the gas phase, the 9H-adenine tautomer predominantly exists.<ref>{{cite journal |journal=Phys.Chem.Chem.Phys. |year=2002 |volume=4 |issue=20 |pages=4877–4882 |title=Tautomers and electronic states of jet-cooled adenine |author=Plützer, Chr., Kleinermanns, K. |doi=10.1039/b204595h }}</ref><ref>{{cite journal |title = Infrared spectra studies on purine, adenine, and 2-chloroadenine |journal = Spectrochimica Acta Part A: Molecular Spectroscopy |volume = 50 |pages = 1081–1094 |year = 1994 |doi = 10.1016/0584-8539(94)80030-8 |author = M. J. Nowak et al. }}</ref>
 
== Biosynthesis ==
The [[biosynthetic pathway]] of [[purine metabolism]] gives rise to adenine and [[guanine]], both synthesized from the common precursor [[inosine monophosphate]] ('''IMP'''). The purine ring is built stepwise on a [[ribose phosphate]] backbone, specifically [[5-phosphoribosyl-1-pyrophosphate]] ('''PRPP''').
 
Atoms within the adenine ring originate from several sources:
* [[Glycine]]
* [[Glutamine]]
* [[Aspartic acid]]
* [[Formyl group]]s carried by [[tetrahydrofolate]]
 
== Function ==
Adenine is essential for the formation of nucleic acids:
* In [[DNA]], it pairs with [[thymine]] (A-T) via two hydrogen bonds.
* In [[RNA]], it pairs with [[uracil]] (A-U).


==Biosynthesis==
Adenine is also involved in the formation of various [[nucleoside]]s and [[nucleotide]]s:
The metabolic pathway of [[Purine metabolism]] oversees the formation of both adenine and [[guanine]]. These nucleobases trace back to the nucleotide [[inosine monophosphate]] (IMP). This nucleotide is synthesized on a pre-existing [[ribose phosphate]] backbone. The pathway incorporates atoms from amino acids like [[glycine]], [[glutamine]], and [[aspartic acid]], and it also fuses with the enzyme tetrahydrofolate.
* Adenine + [[ribose]] → [[adenosine]]
* Adenine + [[deoxyribose]] → [[deoxyadenosine]]
* Adenosine + three [[phosphate group]]s → [[adenosine triphosphate]] ('''ATP''')


==Function==
ATP is the primary energy currency of the cell, participating in numerous [[metabolic pathway]]s. Adenine is also integral to the structure of:
Among the purine [[nucleobase]]s, adenine and [[guanine]] are crucial for constructing the [[nucleic acid]]s. In DNA structures, adenine's role is to bind with [[thymine]] through two [[hydrogen bond]]s, ensuring stability. For [[Protein biosynthesis|protein synthesis]] in RNA, adenine pairs with [[uracil]].
* [[NAD]] (nicotinamide adenine dinucleotide)
* [[FAD]] (flavin adenine dinucleotide)
* [[cAMP]] (cyclic adenosine monophosphate), a second messenger


[[File:Base pair AT.svg|200px]]
=== Base Pairing Diagrams ===
[[File:Base pair AU.svg|200px]]
[[File:Base pair AT.svg|200px|thumb|Adenine-Thymine (DNA)]]
[[File:Base pair AD.svg|200px]]
[[File:Base pair AU.svg|200px|thumb|Adenine-Uracil (RNA)]]
[[File:Base pair APsi.svg|200px]]
[[File:Base pair AD.svg|200px|thumb|Adenine-Dihydrouracil (RNA)]]
:'''Pairs:''' A-T (DNA) | A-U (RNA) | A-D (RNA) | A-Ψ (RNA)
[[File:Base pair APsi.svg|200px|thumb|Adenine-Pseudouridine (RNA)]]


When attached to [[ribose]], adenine forms the [[nucleoside]] known as [[adenosine]]. When linked to [[deoxyribose]], it produces [[deoxyadenosine]]. The addition of three [[phosphate group]]s to adenosine results in the formation of [[adenosine triphosphate]] (ATP). This nucleotide is vital in cellular metabolism, facilitating energy transfer between [[chemical reactions]].
== History ==
Adenine was first isolated and named by [[Albrecht Kossel]] in 1885, who derived it from the [[pancreas]]—hence the name from Greek “''aden''” (Ἀδήν), meaning “gland.” Historically, adenine was once classified as '''Vitamin B<sub>4</sub>''', but this designation is now obsolete.


==History==
Notably, adenine forms a structural component of the B-vitamin-derived cofactors:
Historically, adenine was referred to as '''Vitamin B<sub>4</sub>''' in older scientific literature.<ref>{{cite journal |journal=Biochem J. |year=1930 |volume=24 |issue=6 |pages=1827–31 |title=The assay of vitamin B4 |author=Vera Reader }}</ref> Although it is no longer classified as a true vitamin or part of the [[Vitamin B]] complex, it does associate with the B vitamins, [[niacin]] and [[riboflavin]]. These vitamins combine with adenine to create essential cofactors [[nicotinamide adenine dinucleotide]] (NAD) and [[FAD|flavin adenine dinucleotide]] (FAD).
* [[Nicotinamide adenine dinucleotide]] (NAD), from [[niacin]]
* [[Flavin adenine dinucleotide]] (FAD), from [[riboflavin]]


Adenine was named by [[Albrecht Kossel]] in 1885, inspired by the pancreas (in [[Greek language|Greek]], "aden") from which his sample was derived.<ref>[http://www.etymonline.com/index.php?term=adenine Online Etymology Dictionary] by Douglas Harper</ref> Experiments in 1961 revealed that adenine could be synthesized from the [[polymerization]] of [[ammonia]] with five [[hydrogen cyanide]] molecules.<ref>{{cite journal |author=Oró J, Kimball AP |title=Synthesis of adenine from hydrogen cyanide |journal=Archives of biochemistry and biophysics |volume=94|pages=217–27 |year=1961 }}</ref> The implications of these findings on the [[origin of life]] on [[Earth]] are still debated.<ref>{{cite journal |title=The prebiotic role of adenine |first=Robert |last=Shapiro |journal=Origins of Life and Evolution of Biospheres |year=1995 |doi=10.1007/BF01581575 }}</ref>
=== Prebiotic Synthesis ===
Experiments in the 1960s demonstrated that adenine can be synthesized by heating [[ammonia]] with [[hydrogen cyanide]] (HCN), suggesting possible relevance to the [[origin of life]] on [[Earth]].


In 2011, studies on [[meteorites]] suggested that adenine might have extraterrestrial origins, indicating that the building blocks of [[DNA]] and [[RNA]] could form in [[outer space]].<ref>{{cite web |title=Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases |url=http://www.pnas.org/content/early/2011/08/10/1106493108 |publisher=[[PNAS]] |year=2011 }}</ref>
In 2011, studies of [[carbonaceous chondrite]] [[meteorites]] revealed the presence of adenine and other nucleobases, indicating that these biologically relevant molecules may form in [[outer space]] and be delivered to early Earth via [[extraterrestrial]] means.


==References==
== See also ==
{{reflist}}
* [[Purine]]
* [[Nucleic acid]]
* [[DNA replication]]
* [[RNA polymerase]]
* [[Nucleoside]]
* [[Nucleotide]]
* [[ATP]]
* [[Cofactor (biochemistry)]]
* [[Vitamin B complex]]


==External links==
== External links ==
* [http://gmd.mpimp-golm.mpg.de/Spectrums/f082d045-7938-4e4e-8841-1d748bccc768.aspx Vitamin B4 MS Spectrum]
* [http://gmd.mpimp-golm.mpg.de/Spectrums/f082d045-7938-4e4e-8841-1d748bccc768.aspx Vitamin B4 MS Spectrum – Golm Metabolome Database]
{{Nucleobases, nucleosides, and nucleotides}}
{{Nucleobases, nucleosides, and nucleotides}}
{{Vitamin}}
{{Vitamin}}
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[[Category:Purines]]
[[Category:Purines]]
[[Category:Vitamins]]
[[Category:Vitamins]]
[[Category:Biochemistry]]
[[Category:Molecular biology]]
[[Category:Genetics]]

Latest revision as of 01:42, 31 March 2025

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Numbered structure of adenine.

Adenine (A, Ade) is a nucleobase classified as a purine derivative, and plays a critical role in numerous biochemical processes. It is a key component of both DNA and RNA, as well as several essential cofactors and cellular energy molecules.

Overview[edit]

Adenine is fundamental in cellular respiration, forming part of adenosine triphosphate (ATP), the principal molecule for storing and transferring chemical energy in cells. It is also present in the important cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD).

In the context of genetic material, adenine is one of the four nucleobases in DNA, where it forms base pairs with thymine through hydrogen bonds. In RNA, adenine pairs with uracil during transcription and protein biosynthesis.

Structure[edit]

Adenine is a heterocyclic compound composed of a fused imidazole and pyrimidine ring—together forming the purine structure. It exists in several tautomeric forms, which interconvert rapidly in aqueous solutions. The predominant tautomer under isolated conditions (e.g., in the gas phase or inert matrices) is the 9H-adenine.

Biosynthesis[edit]

The biosynthetic pathway of purine metabolism gives rise to adenine and guanine, both synthesized from the common precursor inosine monophosphate (IMP). The purine ring is built stepwise on a ribose phosphate backbone, specifically 5-phosphoribosyl-1-pyrophosphate (PRPP).

Atoms within the adenine ring originate from several sources:

Function[edit]

Adenine is essential for the formation of nucleic acids:

  • In DNA, it pairs with thymine (A-T) via two hydrogen bonds.
  • In RNA, it pairs with uracil (A-U).

Adenine is also involved in the formation of various nucleosides and nucleotides:

ATP is the primary energy currency of the cell, participating in numerous metabolic pathways. Adenine is also integral to the structure of:

  • NAD (nicotinamide adenine dinucleotide)
  • FAD (flavin adenine dinucleotide)
  • cAMP (cyclic adenosine monophosphate), a second messenger

Base Pairing Diagrams[edit]

Adenine-Thymine (DNA)
Adenine-Uracil (RNA)
Adenine-Dihydrouracil (RNA)
Adenine-Pseudouridine (RNA)

History[edit]

Adenine was first isolated and named by Albrecht Kossel in 1885, who derived it from the pancreas—hence the name from Greek “aden” (Ἀδήν), meaning “gland.” Historically, adenine was once classified as Vitamin B4, but this designation is now obsolete.

Notably, adenine forms a structural component of the B-vitamin-derived cofactors:

Prebiotic Synthesis[edit]

Experiments in the 1960s demonstrated that adenine can be synthesized by heating ammonia with hydrogen cyanide (HCN), suggesting possible relevance to the origin of life on Earth.

In 2011, studies of carbonaceous chondrite meteorites revealed the presence of adenine and other nucleobases, indicating that these biologically relevant molecules may form in outer space and be delivered to early Earth via extraterrestrial means.

See also[edit]

External links[edit]

Nucleic acid constituents
Nucleobase
Nucleoside
Nucleotide
(Nucleoside monophosphate)
Nucleoside diphosphate
Nucleoside triphosphate



Vitamins[edit]

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I[edit]

K[edit]

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N[edit]

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