Tuesday, August 28, 2007

Adenine

Adenine

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For the programming language Adenine, see Adenine (programming language).

Adenine
Systematic (IUPAC) name
7H-purin-6-amine
Synonyms
6-aminopurine
Identifiers
CAS number 73-24-5
PubChem 190
Chemical data
Formula C5H5N5
Mol. weight 135.127
SMILES Nc1ncnc2[nH]cnc12
Physical data
Melt. point 360 - 365 °C (-265 °F)
Complete data

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.

Contents

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[edit] Structure

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

[edit] Function

Adenine is one of the two purine nucleobases 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.

[edit] History

In older literature, adenine was sometimes called Vitamin B4[1]. It is no longer considered a true vitamin nor part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors NAD and 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.[2]

[edit] External links


[edit] References

  1. ^ Vera Reader (1930). "The assay of vitamin B4". Biochem J. 24 (6): 1827–31..
  2. ^ Shapiro, Robert (June, 1995). "The prebiotic role of adenine: A critical analysis". Origins of Life and Evolution of Biospheres 25: 83-98. DOI:10.1007/BF01581575.


v • d • e
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: Types of Nucleic Acids Analogues of nucleic acids:
Nucleobases: Purine (Adenine, Guanine) | Pyrimidine (Uracil, Thymine, Cytosine)
Nucleosides: Adenosine/Deoxyadenosine | Guanosine/Deoxyguanosine | Uridine | Thymidine | Cytidine/Deoxycytidine
Nucleotides: monophosphates (AMP, UMP, GMP, CMP) | diphosphates (ADP, UDP, GDP, CDP) | triphosphates (ATP, UTP, GTP, CTP) | cyclic (cAMP, cGMP, cADPR)
Deoxynucleotides: monophosphates (dAMP, TMP, dGMP, dCMP) | diphosphates (dADP, TDP, dGDP, dCDP) | triphosphates (dATP, TTP, dGTP, dCTP)
Ribonucleic acids: RNA | mRNA | piRNA | tRNA | rRNA | ncRNA | gRNA | shRNA | siRNA | snRNA | miRNA | snoRNA
Deoxyribonucleic acids: DNA | mtDNA | cDNA | plasmid | Cosmid | BAC | YAC | HAC
Analogues of nucleic acids: GNA | PNA | TNA | Morpholino | LNA
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