Which Components Bond With Adenine

Chemical compound in Dna and RNA

Adenine

Names

Preferred IUPAC proper name

9H-Purin-6-amine

Other names

6-Aminopurine

Identifiers

CAS Number

73-24-5 ^Y

3D model (JSmol)

Interactive paradigm
Interactive image

Beilstein Reference

608603

ChEBI

CHEBI:16708 ^Y

ChEMBL

ChEMBL226345 ^Y

ChemSpider

185 ^Y

DrugBank

DB00173 ^Y

ECHA InfoCard

100.000.724

EC Number

200-796-1

Gmelin Reference

3903

IUPHAR/BPS

4788

KEGG

D00034 ^Y

PubChem CID

RTECS number

AU6125000

UNII

JAC85A2161 ^Y

CompTox Dashboard (EPA)

DTXSID6022557

InChI

InChI=1S/C5H5N5/c6-4-3-five(9-1-vii-three)10-2-viii-4/h1-2H,(H3,6,7,8,9,10)^Y

Primal: GFFGJBXGBJISGV-UHFFFAOYSA-North^Y
InChI=ane/C5H5N5/c6-4-three-5(9-ane-7-3)x-2-8-4/h1-2H,(H3,vi,7,8,9,10)

Key: GFFGJBXGBJISGV-UHFFFAOYAT

SMILES

NC1=NC=NC2=C1N=CN2
Nc1c2ncNc2ncn1

Properties

Chemical formula

C ₅ H _v N ₅

Molar mass

135.13 g/mol

Appearance

white to low-cal yellowish, crystalline

Density

i.6 g/cm^three (calculated)

Melting signal

360 to 365 °C (680 to 689 °F; 633 to 638 Yard) decomposes

Solubility in water

0.103 g/100 mL

Solubility

negligible in ethanol, soluble in hot h2o and/or aqua ammonia

Acidity (pG _a)

4.15 (secondary), 9.eighty (chief)^[1]

Thermochemistry

Oestrus capacity (C)

147.0 J/(K·mol)

Std enthalpy of
germination (Δ_f H ^⦵ ₂₉₈)

96.9 kJ/mol

Hazards

Lethal dose or concentration (LD, LC):

LD_l (median dose)

227 mg/kg (rat, oral)

Safe data sheet (SDS)

MSDS

Except where otherwise noted, data are given for materials in their standard country (at 25 °C [77 °F], 100 kPa).

Yverify (what is^{Y North} ?)

Infobox references

Chemic compound

Adenine () (symbol A or Ade) is a nucleobase (a purine derivative). It is one of the iv nucleobases in the nucleic acrid of DNA that are represented by the messages G–C–A–T. The 3 others are guanine, cytosine and thymine. Its derivatives have a diverseness 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), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and equally a chemical component of Deoxyribonucleic acid and RNA.^[two] The shape of adenine is complementary to either thymine in Dna or uracil in RNA.

The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen (thereby removing the existing hydrogen cantlet). The remaining construction is chosen an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose, as used in RNA and ATP; deoxyadenosine is adenine attached to deoxyribose, as used to form Dna.

Construction [edit]

Adenine construction, with standard numbering of positions in red.

Adenine forms several tautomers, compounds that can be apace interconverted and are oftentimes considered equivalent. However, in isolated atmospheric condition, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.^[three] ^[4]

Biosynthesis [edit]

Purine metabolism involves the formation of adenine and guanine. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP), which in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acrid, as well equally the coenzyme tetrahydrofolate.

Manufacturing method [edit]

Patented Aug. 20, 1968, the current recognized method of industrial-scale production of adenine is a modified grade of the formamide method. This method heats upwardly formamide under 120 degree Celsius conditions inside a sealed flask for 5 hours to form adenine. The reaction is heavily increased in quantity by using a phosphorus oxychloride (phosphoryl chloride) or phosphorus pentachloride every bit an acid catalyst and sunlight or ultraviolet atmospheric condition. After the five hours have passed and the formamide-phosphorus oxychloride-adenine solution cools down, water is put into the flask containing the formamide and now-formed adenine. The water-formamide-adenine solution is then poured through a filtering cavalcade of activated charcoal. The water and formamide molecules, beingness small molecules, will pass through the charcoal and into the waste flask; the large adenine molecules, withal, will attach or "adsorb" to the charcoal due to the van der Waals forces that interact betwixt the adenine and the carbon in the charcoal. Because charcoal has a large surface area, it's able to capture the majority of molecules that pass a certain size (greater than water and formamide) through information technology. To excerpt the adenine from the charcoal-adsorbed adenine, ammonia gas dissolved in water (aqua ammonia) is poured onto the activated charcoal-adenine structure to liberate the adenine into the ammonia-h2o solution. The solution containing water, ammonia, and adenine is then left to air dry out, with the adenine losing solubility due to the loss of ammonia gas that previously made the solution basic and capable of dissolving adenine, thus causing information technology to crystallize into a pure white powder that can be stored.^[5]

Part [edit]

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 assistance in stabilizing the nucleic acrid structures. In RNA, which is used for poly peptide synthesis, adenine binds to uracil.

Adenine forms adenosine, a nucleoside, when fastened to ribose, and deoxyadenosine when fastened to deoxyribose. It forms adenosine triphosphate (ATP), a nucleoside triphosphate, when 3 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 [edit]

Adenine on Crick and Watson'south Dna molecular model, 1953. The motion-picture show is shown upside down compared to well-nigh modern drawings of adenine, such as those used in this article.

In older literature, adenine was sometimes chosen Vitamin B₄ .^[6] Due to it being synthesized by the trunk and not essential to exist obtained by diet, it does not meet the definition of vitamin and is no longer part of the Vitamin B circuitous. However, two B vitamins, niacin and riboflavin, bind with adenine to grade 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 after Greek ἀδήν aden "gland", in reference to the pancreas, from which Kossel's sample had been extracted.^[seven] ^[8]

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

On August 8, 2011, a report, based on NASA studies with meteorites establish on Globe, was published suggesting edifice blocks of DNA and RNA (adenine, guanine and related organic molecules) may have been formed extraterrestrially in outer space.^[11] ^[12] ^[13] 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 lite is much more complicated than previously thought"; these findings take implications for spectroscopic measurements of heterocyclic compounds, according to 1 report.^[14]

References [edit]

^ Dawson, R.M.C., et al., Data for Biochemical Inquiry, Oxford, Clarendon Press, 1959.
^ Definition of Adenine from the Genetics Habitation Reference - National Institutes of Wellness
^ Plützer, Chr.; Kleinermanns, K. (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy". Phys. Chem. Chem. Phys. four (20): 4877–4882. Bibcode:2002PCCP....four.4877P. doi:10.1039/b204595h.
^ K. J. Nowak; H. Rostkowska; L. Lapinski; J. S. Kwiatkowski; J. Leszczynski (1994). "Experimental matrix isolation and theoretical ab initio HF/6-31G(d, p) studies of infrared spectra of purine, adenine and ii-chloroadenine". Spectrochimica Acta Office A: Molecular Spectroscopy. 50 (half-dozen): 1081–1094. Bibcode:1994AcSpA..fifty.1081N. doi:ten.1016/0584-8539(94)80030-8. ISSN 0584-8539.
^ [1], "Process for preparing adenine", issued 1966-11-x
^ Reader Five (1930). "The analysis of vitamin B(4)". The Biochemical Journal. 24 (6): 1827–31. doi:10.1042/bj0241827. PMC1254803. PMID 16744538.
^ A. Kossel (1885) "Ueber eine neue Base aus dem Thierkörper" (On a new base from the animate being trunk), 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.)
^ Online Etymology Dictionary past Douglas Harper
^ Oro J, Kimball AP (August 1961). "Synthesis of purines nether possible archaic earth weather condition. I. Adenine from hydrogen cyanide". Archives of Biochemistry and Biophysics. 94 (2): 217–27. doi:x.1016/0003-9861(61)90033-ix. PMID 13731263.
^ Shapiro, Robert (June 1995). "The prebiotic function of adenine: A critical analysis". Origins of Life and Evolution of Biospheres. 25 (1–3): 83–98. Bibcode:1995OLEB...25...83S. doi:10.1007/BF01581575. PMID 11536683. S2CID 21941930.
^ Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, Business firm CH, Dworkin JP (Aug 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National University of Sciences of the United States of America. 108 (34): 13995–8. Bibcode:2011PNAS..10813995C. doi:10.1073/pnas.1106493108. PMC3161613. PMID 21836052.
^ Steigerwald, John (8 Baronial 2011). "NASA Researchers: DNA Building Blocks Can Exist Made in Space". NASA. Retrieved 2011-08-10 .
^ ScienceDaily Staff (ix August 2011). "Dna Edifice Blocks Can Be Made in Infinite, NASA Prove Suggests". ScienceDaily . Retrieved 2011-08-09 .
^
Williams P (August 18, 2011). "Physicists Uncover New Data On Adenine, a Crucial Building Block of Life". Science Daily . Retrieved 2011-09-01 .
- Barbatti Thou, Ullrich S (2011). "Ionization potentials of adenine along the internal conversion pathways". Physical Chemistry Chemical Physics. 13 (34): 15492–15900. Bibcode:2011PCCP...1315492B. doi:10.1039/C1CP21350D. PMID 21804965.