Adenine: Wikis

  

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Adenine
Identifiers
CAS number 73-24-5 Yes check.svgY
PubChem 190
ChemSpider 185
SMILES
InChI
InChI key GFFGJBXGBJISGV-UHFFFAOYAT
Properties
Molecular formula C5H5N5
Molar mass 135.13 g/mol
Melting point

360–65 °C

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Adenine is a nucleobase (a purine derivative) 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.[1] The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

Contents

Structure

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

Biosynthesis

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 ribosome through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as fused with the enzyme tetrahydrofolate.

In Saccharomyces cerevisiae (yeast), the adenine pathway converts P-ribosyl-PP into adenine through a seven-step process.

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 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.[2] 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. Hermann Emil Fischer was one of the early scientists to study adenine.

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.[3]

References

  1. ^ Definition of Adenine from the Genetics Home Reference - National Institutes of Health
  2. ^ Vera Reader (1930). "The assay of vitamin B4". Biochem J. 24 (6): 1827–31.. doi:10.1007/BF01581575. 
  3. ^ 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. http://www.springerlink.com/content/ru56122875200030/. 

1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

ADENINE, or 6-AMINO-PURIN, C5H5N5, in chemistry, a basic substance which has been obtained as a decomposition product of nuclein, and also from the pancreatic glands of oxen. It has been synthesized by E. Fischer (Berichte, 1897, 30, p. 2238) by heating 2.6.8-trichlorpurin with 10 times its weight of ammonia for six hours at 100° C.; by this means 6-amino-2.8-dichlorpurin is obtained, which on reduction by means of hydriodic acid and phosphonium iodide is converted into adenine. In 1898 E. Fischer also obtained it from 8-oxy-2.6-dichlorpurin (Berichte, 1898, 31, p. 104). It crystallizes in long needles; forms salts C5H5N5.2HI and (C5H5N5)2.H2SO4.2H2O, and is converted by nitrous acid into hypoxanthine or 6-oxypurin. On heating with hydrochloric acid at 180-200° C. it is decomposed; the products of the reaction being glycocoll, ammonia, formic acid and carbon dioxide. Various methyl derivatives of adenine have been described by E. Fischer (Berichte, 1898, 31, p. 104) and by M. Kruger (Zeit. für physiol. Chemie, 1894, 18, p. 434). For the constitution of adenine see Purin.


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Simple English

File:Adé
Adenine Chemical Structure

Adenine is a chemical part of DNA and RNA.

It places several tautomers together. These are compounds that can be quickly changed and are often thought of as the same. It is a purine.

Contents

Function

In DNA, adenine sticks to thymine with two hydrogen bonds to help in making the nucleic acid structures stronger. In RNA, which is used in the cytoplasm for protein synthesis, adenine sticks to uracil.

History

In older books, 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]

References

  1. Vera Reader (1930). [Expression error: Unexpected < operator "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. http://www.springerlink.com/content/ru56122875200030/. 

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