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Adenine /ˈædᵻnᵻn/ (A, Ade) is a nucleobase (a purine derivative). Its derivatives have 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). It also has functions in protein synthesis and as a chemical component of DNA and RNA.^[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

The image on the right shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen, so removing the hydrogen. The remaining structure is called an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose as used in RNA and ATP; deoxyadenosine, adenine attached to deoxyribose, as is used to form DNA.

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 in turn is synthesized from a pre-existing ribose phosphate through a complex pathway using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as 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 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 nucleoside triphosphate, 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

Adenine on Crick and Watson’s DNA molecular model, 1953. The picture is shown upside down compared to most modern drawings of adenine, such as those used in this article.

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.^[why?] 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 NASA studies with meteorites found on Earth, was published suggesting building blocks of DNA and RNA (adenine, guanine and related organic molecules) may have been formed extraterrestrially in 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

^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ Definition of Adenine from the Genetics Home Reference - National Institutes of Health
^ Plützer, Chr.; Kleinermanns, K. (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy". Phys.Chem.Chem.Phys. 4 (20): 4877–4882. Bibcode:2002PCCP....4.4877P. doi:10.1039/b204595h.
^ M. 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 2-chloroadenine,". Spectrochimica Acta Part A: Molecular Spectroscopy. 50 (6): 1081–1094. Bibcode:1994AcSpA..50.1081N. ISSN 0584-8539. doi:10.1016/0584-8539(94)80030-8.
^ Reader V (1930). "The assay of vitamin B(4)". The Biochemical Journal. 24 (6): 1827–31. PMC 1254803 . PMID 16744538. doi:10.1042/bj0241827.
^ 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.)
^ Online Etymology Dictionary by Douglas Harper
^ Oro 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. PMID 13731263. doi:10.1016/0003-9861(61)90033-9.
^ Shapiro, Robert (June 1995). "The prebiotic role of adenine: A critical analysis". Origins of Life and Evolution of Biospheres. 25 (1–3): 83–98. Bibcode:1995OLEB...25...83S. doi:10.1007/BF01581575.
^ Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP (Aug 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National Academy of Sciences of the United States of America. 108 (34): 13995–8. PMC 3161613 . PMID 21836052. doi:10.1073/pnas.1106493108.
^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.
^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence 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. journal reference: Mario Barbatti, Susanne Ullrich. Ionization potentials of adenine along the internal conversion pathways. Physical Chemistry Chemical Physics, 2011; doi:10.1039/C1CP21350D -- a University of Georgia physicist and a collaborator in Germany have shown that ... adenine, has an unexpectedly variable range of ionization energies along its reaction pathways....

External links

Vitamin B4 MS Spectrum

English Journal

Functional surface engineering of quantum dot hydrogels for selective fluorescence imaging of extracellular lactate release.

Zhang X1, Ding S1, Cao S1, Zhu A2, Shi G1.
Biosensors & bioelectronics.Biosens Bioelectron.2016 Jun 15;80:315-22. doi: 10.1016/j.bios.2016.01.083. Epub 2016 Jan 30.
Selective and sensitive detection of extracellular lactate is of fundamental significance for studying the metabolic alterations in tumor progression. Here we report the rational design and synthesis of a quantum-dot-hydrogel-based fluorescent probe for biosensing and bioimaging the extracellular la
PMID 26852200

DNA methyltransferase detection based on digestion triggering the combination of poly adenine DNA with gold nanoparticles.

Liu P1, Wang D1, Zhou Y1, Wang H1, Yin H2, Ai S3.
Biosensors & bioelectronics.Biosens Bioelectron.2016 Jun 15;80:74-8. doi: 10.1016/j.bios.2015.12.100. Epub 2015 Dec 29.
DNA methyltransferase (MTase) has received a large amount of attention due to its catalyzation of DNA methylation in both eukaryotes and prokaryotes, which has a close relationship to cancer and bacterial diseases. Herein, a novel electrochemical strategy based on Dpn I digestion triggering the comb
PMID 26807517

Electrochemical examination of ability of dsDNA/PAM composites for storing and releasing of doxorubicin.

Zabost E1, Liwinska W2, Karbarz M2, Kurek E2, Lyp M3, Donten M2, Stojek Z2.
Bioelectrochemistry (Amsterdam, Netherlands).Bioelectrochemistry.2016 Jun;109:1-8. doi: 10.1016/j.bioelechem.2015.12.001. Epub 2015 Dec 2.
Composites consisting of ss- and ds-DNA strands and polyacrylamide (PAM) hydrogel have been synthesized. DNA was entrapped non-covalently. The obtained DNA biomaterial exhibited a strong increase in guanine and adenine anodic currents when temperature reached the physiological level. This increase w
PMID 26764570

Japanese Journal

Magnetic Properties of Copper(II) Complexes of 6-Aminopurine and 6-Hydroxypurine

Bulletin of the Chemical Society of Japan 45(4), 1054-1057, 1972
NAID 130001975362

しいたけの血漿コレステロール低下作用物質の単離 (速報)

栄養と食糧 23(3), 218-221, 1970
NAID 130003682014

Studies on the Purine-sensitive Mutants of <i>Bacillus subtilis</i>:I. Properties of an Adenosine-sensitive Mutant

The Journal of Biochemistry 66(4), 487-492, 1969
NAID 130003418677

Related Pictures

read more 6 benzyl aminopurine only 2 Hydroxy 6 aminopurine 98 250mg de Croissance » 6-aminopurine (Adénine Cl-6-Aminopurine, 2-Cl-Adenine Aminopurine, (A)) in studies of proteins of 2-halo-6-aminopurine derivatives 73-24-5 | Adenine (6-Aminopurine)

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リンク元

「アデニン」

Adenine
Names
	IUPAC name 9H-purin-6-amine
	Other names 6-aminopurine
Identifiers
CAS Number	73-24-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:16708 ;
ChemSpider	185 ;
DrugBank	DB00173 ;
ECHA InfoCard	100.000.724
EC Number	200-796-1
IUPHAR/BPS	4788;
KEGG	D00034 ;
PubChem CID	190;
RTECS number	AU6125000
UNII	JAC85A2161 ;
	InChI InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) Key: GFFGJBXGBJISGV-UHFFFAOYSA-N ; InChI=1/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) Key: GFFGJBXGBJISGV-UHFFFAOYAT ;
	SMILES NC1=NC=NC2=C1N=C[N]2 ; Nc1ncnc2[nH]cnc12 ;
Properties
Chemical 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) decomposes
Solubility in water	0.103 g/100 mL
Solubility	negligible in ethanol
Acidity (pKa)	4.15 (secondary), 9.80 (primary)
Thermochemistry
Specific; heat capacity (C)	147.0 J/(K·mol)
Std enthalpy of; formation (ΔfHo298)	96.9 kJ/mol
Hazards
Safety data sheet	MSDS
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	227 mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: adenine Ade
同: 6-アミノプリン 6-aminopurine
商: ロイコン; (採血バック)：カーミAMAP液、カーミCA液、カーミCリューコトラップMAP、セパセルインテグラC-MAP、セパセルインテグラCA、セパセルインテグラMAP、テルモ血液バッグCPDA、テルモ血液バッグMAP液
関: プリン、プリン塩基

核酸のプリン塩基の一種。

[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. (2002). "Tautomers and electronic states of jet-cooled adenine investigated by double resonance spectroscopy". Phys.Chem.Chem.Phys. 4 (20): 4877–4882. Bibcode:2002PCCP....4.4877P. doi:10.1039/b204595h.

[4] M. 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 2-chloroadenine,". Spectrochimica Acta Part A: Molecular Spectroscopy. 50 (6): 1081–1094. Bibcode:1994AcSpA..50.1081N. ISSN 0584-8539. doi:10.1016/0584-8539(94)80030-8.

[5] Reader V (1930). "The assay of vitamin B(4)". The Biochemical Journal. 24 (6): 1827–31. PMC 1254803 . PMID 16744538. doi:10.1042/bj0241827.

[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] Oro 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. PMID 13731263. doi:10.1016/0003-9861(61)90033-9.

[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. Bibcode:1995OLEB...25...83S. doi:10.1007/BF01581575.

[Callahan-10] Callahan MP, Smith KE, Cleaves HJ, Ruzicka J, Stern JC, Glavin DP, House CH, Dworkin JP (Aug 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National Academy of Sciences of the United States of America. 108 (34): 13995–8. PMC 3161613 . PMID 21836052. doi:10.1073/pnas.1106493108.

[Steigerwald-11] Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.

[DNA-12] ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09.

[twsA35-13] Williams P (August 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; doi:10.1039/C1CP21350D -- a University of Georgia physicist and a collaborator in Germany have shown that ... adenine, has an unexpectedly variable range of ionization energies along its reaction pathways....

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案内

案内

6-aminopurine