Adenine
- 9H- purine -6 -amine ( IUPAC name)
- 6- aminopurine
A11HA
Light yellow solid
Fixed
Sublimation at 220 ° C.
Decomposition from 360 ° C
Poorly in water
Risk
227 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Adenine (A, Ade) is one of the four main nucleobases in DNA and RNA, along with cytosine, guanine and thymine ( uracil in RNA). Is a heterocyclic organic compound with a purine basic structure and an amino group in the 6-position. The nucleosides of adenine are the deoxyadenosine in DNA and adenosine in the RNA. In the Watson -Crick base pairing, it forms two hydrogen bonds with thymine or uracil.
Representation
- Lord Todd synthesis applied to formamidine and Phenylazomalononitril.
- Adenine can be regarded as a pentamer of cyanide and are presented in liquid ammonia, with yields of over 20% of this.
Biological Significance
Adenine may be part of the DNA, RNA, or various nucleosides and nucleotides.
Nucleosides
About the N9 atom of the five-membered ring of adenine can be bound N- glycosidically linked to the C1 atom of the ribose; this is called a nucleoside, adenosine. When bound to deoxyribose nucleoside produced deoxyadenosine. Synthetic vidarabine contains - in contrast to most nucleosides - instead of ribose, arabinose.
Nucleotides
Arise on adenosine phosphoric acid can be bound as phosphate residue, so
- Adenosine monophosphate ( AMP)
- Adenosine diphosphate ( ADP)
- Adenosine triphosphate ( ATP)
Corresponding molecules are formed when the phosphate residues are bonded to deoxyadenosine ( dAMP, dADP, dATP ).
Adenosine triphosphate ( ATP) plays a special role in the energy metabolism of the cell. By the reaction ATP → ADP P energy is released by the reaction ADP P → ATP energy is stored chemically.
Cyclic adenosine monophosphate ( cAMP) is a very common second messenger in cellular signal transduction.
Adenine is also part of the Nicotinamidadenindinucleotids NAD , which acts as a coenzyme of the hydrogen transfer and is thus involved in the cell in the redox reactions. Adenine is used for the biosynthesis of the coenzyme S- adenosyl- methionine, which finds use in biological methylations.
Part of the DNA and RNA
Adenine forms in the DNA double helix consists of two hydrogen bonds with thymidine. In transcription, however, the adenine of codogenic strand of DNA with the uridine mRNA just formed pairs. In the tRNA, there are also pairs with dihydrouridine or pseudouridine.