Adenine

Structural formula
General
Surname	Adenine
other names	9 H -purine-6-amine ( IUPAC name); 6-aminopurine; ADENINE ( INCI ) ;
Molecular formula	C 5 H 5 N 5
Brief description	light yellow solid
External identifiers / databases
EC number	200-796-1
ECHA InfoCard	100,000,724
PubChem	190
ChemSpider	185
DrugBank	DB00173
Wikidata	Q15277
Drug information
ATC code	A11 HA
properties
Molar mass	135.13 g mol −1
Physical state	firmly
boiling point	Decomposition from 360 ° C
Sublimation point	220 ° C
solubility	poor in water (0.5 g l −1 at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 301 + 310 + 330
Toxicological data	227 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adenine is one of the four nucleobases in DNA and in RNA , alongside cytosine , guanine and thymine or uracil (in RNA).

It is a heterocyclic organic compound with a purine backbone and an amino group in the 6-position. The deoxyadenosine in DNA and the adenosine in RNA are nucleosides that contain adenine. With thymine or uracil it forms two hydrogen bonds in the Watson-Crick base pairing .

presentation

Lord Todd synthesis applied to formamidine and phenylazomalononitrile .
Adenine can be viewed as a pentamer of hydrocyanic acid and can be prepared from it in liquid ammonia with yields of over 20%.

History and biological meaning

On January 12, 1885, the later Nobel Prize winner Albrecht Kossel reported to the Berlin Chemical Society about an important discovery. He was able to isolate a nitrogen-rich base with the empirical formula C ₅ H ₅ N ₅ , for which he derived from the Greek , from a large amount of bovine pancreas, which had been processed by Adolph Bannow (1844-1919) in the Berlin chemical plant Kahlbaum Word "aden" for gland, the name adenine suggested. Kossel also proved it to be a cleavage product of the yeast nuclein. He was later able to detect adenine as a cleavage product of the nucleic acid.

Adenine can be part of DNA, RNA or various nucleosides and nucleotides .

Nucleosides

Via the N ⁹ atom of the five-membered ring, adenine can be bound N -glycosidically to the C ¹ atom of the ribose ; one then speaks of a nucleoside , the adenosine . When binding to deoxyribose , the nucleoside deoxyadenosine is formed . In contrast to most nucleosides, the synthetic vidarabine contains arabinose instead of ribose .


Adenosine, A.	Deoxyadenosine, dA	Vidarabin, araA

Nucleotides

Phosphoric acid can be bound to adenosine as a phosphate residue, which is how it is formed

Corresponding molecules are formed when the phosphate residues are bound to deoxyadenosine (dAMP; dADP; dATP).

Adenosine triphosphate (ATP) plays a special role in the cell's energy metabolism . The reaction ATP → ADP + P releases energy ; the reaction ADP + P → ATP stores energy chemically.

Cyclic adenosine monophosphate (cAMP) is a very common second messenger for cellular signal transduction .

Adenine is also part of the nicotinamide adenine dinucleotide NAD ⁺ , which serves as a coenzyme for hydrogen transfer and thus participates in redox reactions in the cell . Adenine is used for the biosynthesis of the coenzyme S-adenosyl-methionine , which is used in biological methylations , e.g. B. by a Dam methylase .

Part of DNA and RNA

Adenine forms two hydrogen bonds with thymidine in the DNA double helix . During transcription, however, the adenine of the codogenic strand of DNA pairs with the uridine of the mRNA that has just been formed . There are also pairings with dihydrouridine or pseudouridine in the tRNA .


AT base pair (DNA)	AU base pair (RNA)	AD base pair (RNA)	A Ψ base pair (RNA)

Web links

Commons : Adenine - Collection of images, videos and audio files

Commons : Adenine derivatives - collection of images, videos and audio files

Wiktionary: Adenine - explanations of meanings, word origins, synonyms, translations

Entry for adenines in the Human Metabolome Database (HMDB) , accessed November 19, 2013.

Individual evidence

↑ entry to ADENINE in CosIng database of the European Commission, accessed on 27 March 2020th

↑ Adenine data sheet (PDF) from Carl Roth , accessed on December 14, 2010.

↑ ^a ^b entry on adenine. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.

↑ ^a ^b ^c Entry on adenine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

↑ Adenine data sheet from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).

^ Albert Gossauer, Structure and Reactivity of Biomolecules: An Introduction to Organic Chemistry, Verlag Helvetica Chimica Acta, 2006 .

↑ Kossel, A .: About a new base from the animal body. Lecture in: Reports of the German Chemical Society , Issue 18, 1885, p. 79.

^ Kossel, A .: Further contributions to the chemistry of the cell nucleus. In: Zeitschrift für Physiologische Chemie , Volume 10, 1886, p. 248.

↑ Kossel, A .: About the chemical composition of the cell. Lecture in: Archives for Anatomy and Physiology. Physiological Department , 1891, p. 178.

[CosIng-1] try to ADENINE in CosIng database of the European Commission, accessed on 27 March 2020th


1-methyladenine	2-methyladenine	N ⁶ -methyladenine	N ⁶ , N ⁶ -dimethyladenine	N ⁶ isopentenyladenine	2-aminopurine (isoadenine)