Adenine

chembox
ImageFile1 = Adenine chemical structure.png ImageSize1 = 150px
ImageFileL2 = Adenine-3D-balls.png ImageSizeL2 = 100px
ImageFileR2 = Adenine-3D-vdW.png ImageSizeR2 = 100px
IUPACName = 9H-purin-6-amine
OtherNames = 6-aminopurine
Section1 = Chembox Identifiers
CASNo = 73-24-5
PubChem = 190
SMILES = Nc1ncnc2 [nH] cnc12
MeSHName =
Section2 = Chembox Properties
Formula = C₅H₅N₅
MolarMass = 135.127 g/mol
Appearance =
Density =
MeltingPt = 360 - 365 °C
BoilingPt = Adenosine triphosphate is a type of energy
Section3 = Chembox Hazards
Solubility =
MainHazards =
FlashPt =
Autoignition =

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. [ [http://ghr.nlm.nih.gov/ghr/glossary/adenine Definition of Adenine from the Genetics Home Reference] - National Institutes of Health] the shape of adenine is complementary to either thymine or uracil.

tructure

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

Biosynthesis

The Purine metabolism involves the formation of Adenine and Guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which is synthesised on a pre-existing ribose through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as formate ions transferred from the coenzyme tetrahydrofolate.

Function

Adenine is one of the two purine nucleobases (the other being guanine) 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.

History

In older literature, adenine was sometimes called Vitamin B4. [cite journal
journal=Biochem J.
year=1930
volume=24
issue=6
pages=1827–31.
title=The assay of vitamin B4
author=Vera Reader
doi=10.1007/BF01581575] It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (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.Fact|date=May 2008 However, this has been criticized by some chemists. [cite journal
title=The prebiotic role of adenine: A critical analysis
first=Robert
last=Shapiro
journal=Origins of Life and Evolution of Biospheres
date=June, 1995
doi=10.1007/BF01581575
pages=83–98
volume=25
url=http://www.springerlink.com/content/ru56122875200030/]

References