World Library  
Flag as Inappropriate
Email this Article

Adenine

Article Id: WHEBN0000038571
Reproduction Date:

Title: Adenine  
Author: World Heritage Encyclopedia
Language: English
Subject: List of Y-DNA single-nucleotide polymorphisms, Adenosine triphosphate, Cytosine, Purine analogue, Pyrimidine analogue
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Adenine

Adenine
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
EC number
DrugBank
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
RTECS number AU6125000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C5H5N5
Molar mass 135.13 g/mol
Appearance white to light yellow, crystalline
Density 1.6 g/cm3 (calculated)
Melting point 360 to 365 °C (680 to 689 °F; 633 to 638 K)
Solubility in water 0.103 g/100 mL
Solubility negligible in ethanol
Acidity (pKa) 4.15 (secondary), 9.80 (primary)[1]
Thermochemistry
Specific
heat capacity
C
147.0 J/K·mol
Std enthalpy of
formation
ΔfHo298
96.9 kJ/mol
Hazards
MSDS MSDS
LD50 227 mg/kg (rat, oral)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

Adenine (A, Ade) 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.[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

Structure

Adenine structure, with standard numbering of positions in red.

Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.[3][4]

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 ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as fused with the enzyme 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 for protein synthesis, adenine binds to uracil.

A-T-Base-pair (DNA) A-U-Base-pair (RNA) A-D-Base-pair (RNA) A-Ψ-Base-pair (RNA)

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.

Adenosine, A Deoxyadenosine, dA

History

In older literature, adenine was sometimes called Vitamin B4.[5] 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.

It was named in 1885 by Albrecht Kossel, in reference to the pancreas (a specific gland - in Greek, "aden") from which Kossel's sample had been extracted.[6][7]

Experiments performed in 1961 by Joan Oró have shown that a large quantity of adenine can be synthesized from the polymerization of ammonia with five hydrogen cyanide (HCN) molecules in aqueous solution;[8] whether this has implications for the origin of life on Earth is under debate.[9]

On August 8, 2011, a report, based on outer space.[10][11][12] In 2011, physicists reported that adenine has an "unexpectedly variable range of ionization energies along its reaction pathways" which suggested that "understanding experimental data on how adenine survives exposure to UV light is much more complicated than previously thought"; these findings have implications for spectroscopic measurements of heterocyclic compounds, according to one report.[13]

References

  1. ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. ^ Definition of Adenine from the Genetics Home Reference - National Institutes of Health
  3. ^ Plützer, Chr., Kleinermanns, K.; Kleinermanns (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy". Phys.Chem.Chem.Phys. 4 (20): 4877–4882.  
  4. ^ M. J. Nowak and H. Rostkowska and L. Lapinski and J. S. Kwiatkowski and J. Leszczynski (1994). "Experimental matrix isolation and theoretical ab initio HF/6-31G(d, p) studies of infrared spectra of purine, adenine and 2-chloroadenine,". Spectrochimica Acta Part A: Molecular Spectroscopy 50 (6): 1081–1094.  
  5. ^ Vera Reader (1930). "The assay of vitamin B4". Biochem J. 24 (6): 1827–31.  
  6. ^ A. Kossel (1885) "Ueber eine neue Base aus dem Thierkörper" (On a new base from the animal body), Berichte der Deutschen Chemischen Gesellschaft zu Berlin, 18 : 79-81. From p. 79: "Diese Base, für welche ich den Namen Adenin vorschlage, wurde zunächst aus Pankreasdrüsen vom Rind dargestellt." (This base, for which I suggest the name "adenine", was first prepared from the pancreas glands of steer.)
  7. ^ Online Etymology Dictionary by Douglas Harper
  8. ^ Oró J, Kimball AP (August 1961). "Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide". Archives of biochemistry and biophysics 94 (2): 217–27.  
  9. ^ Shapiro, Robert (June 1995). "The prebiotic role of adenine: A critical analysis". Origins of Life and Evolution of Biospheres 25 (1–3): 83–98.  
  10. ^ Callahan, M.P.; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases".  
  11. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space".  
  12. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests".  
  13. ^ Philip Williams (Aug. 18, 2011). "Physicists Uncover New Data On Adenine, a Crucial Building Block of Life". Science Daily. Retrieved 2011-09-01. journal reference: Mario Barbatti, Susanne Ullrich. Ionization potentials of adenine along the internal conversion pathways. Physical Chemistry Chemical Physics, 2011;  

External links

  • Vitamin B4 MS Spectrum
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.