73-24-5 Usage
Chemical Description
Adenine is a purine base found in DNA and RNA.
Description
adenine is one of the purine nitrogenous bases that composes DNA and RNA; composed of two carbon–nitrogen rings. Adenine bonds with thymine in DNA and with uracil in RNA (see base pairing rule); it is also a major component of other molecules such as adenosine triphosphate.
Chemical Properties
Adenine is a prominent member of the family of naturally occurring purines. Adenine occurs not only in ribonucleic acids (RNA), and deoxyribonucleic acids (DNA), but in nucleosides, such as adenosine, and nucleotides, such as adenylic acid, which may be linked with enzymatic functions quite apart from nucleic acids. Adenine, in the form of its ribonucleotide, is produced in mammals and fowls endogenously from smaller molecules and no nutritional essentiality is ascribed to it. In the nucleosides, nucleotides, and nucleic acids, the attachment or the sugar moiety is at position 9.The purines and pyrimidines absorb ultraviolet light readily, with absorption peaks at characteristic frequencies. This has aided in their identification and quantitative determination.
Physical properties
Adenine is a white to almost white crystalline powder that is an important biological compound found in deoxyribonucleic acid (DNA), ribonucleic acid (RNA), and adenosine triphosphate (ATP). It was once commonly referred to as vitamin B4 but is no longer considered a vitamin. Adenine is derived from purine. Purine is a heterocyclic compound.
History
Adenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.
Uses
Adenine is used as an active component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron. It is useful as a local antiseptic and vitamin B4. Further, it is used in the microbial determination of niacin. It is also employed as a food supplement for adult rats to investigate the effects of dietary adenine overload. In addition to this, it is used in the production of nucleotides of the nucleic acids.
Definition
ChEBI: Adenine is the parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6. It has a role as a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purine nucleobase and a member of 6-aminopurines. It derives from a hydride of a 9H-purine.
Application
Widespread throughout animal and plant tissues combined with niacinamide, d-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coa laninedehydrase. It is used in microbial determination of niacin; in research on heredity, virus diseases, and cancer.
General Description
Adenine is a purine nucleobase. It is part of DNA, and RNA. Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP). It is a nitrogenous base found in DNA and RNA. It is also a constituent of certain coenzymes and when combined with the sugar ribose it forms the nucleoside adenosine found in AMP, ADP, and ATP. Adenine has a purine ring structure. It is one of the major component bases ofnucleotides and the nucleic acidsDNA and RNA.
Biochem/physiol Actions
Adenine is essential for many in vivo and in vitro biochemical processes. Adenine is converted to adenosine with ribose. On phosphorylation, it forms AMP, ADP and ATP. ATP is the energy currency of the cell and is required during cellular metabolism. Adenine is metabolized to is 2,8-dihydroxyadenine, which on accumulation in proximal tubules leads to the induction of chronic kidney disease (CKD) with severe anemia in rats. Adenine based derivatives elicit antiviral functionality against dsDNA viruses and are exploited for generating antiviral scaffolds.
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.
Purification Methods
Crystallise adenine from distilled water. [Beilstein 26 III/IV 3561.]
Check Digit Verification of cas no
The CAS Registry Mumber 73-24-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 3 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 73-24:
(4*7)+(3*3)+(2*2)+(1*4)=45
45 % 10 = 5
So 73-24-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-3H,(H2,6,7,8,9,10)
73-24-5Relevant articles and documents
Using conformationally locked nucleosides to calibrate the anomeric effect: Implications for glycosyl bond stability
Moon, Hyung Ryong,Siddiqui, Maqbool A.,Sun, Guangyu,Filippov, Igor V.,Landsman, Nicholas A.,Lee, Yi-Chien,Adams, Kristie M.,Barchi Jr., Joseph J.,Deschamps, Jeffrey R.,Nicklaus, Marc C.,Kelley, James A.,Marquez, Victor E.
, p. 6707 - 6717 (2010)
Steric and electronic parameters, such as the anomeric effect (AE) and gauche effect play significant roles in steering the North⇆South equilibrium of nucleosides in solution. Two isomeric oxa-bicyclo[3.1.0]hexane nucleosides that are conformational
Plasmonic Hot Electron-Mediated Hydrodehalogenation Kinetics on Nanostructured Ag Electrodes
Liu, Jia,Cai, Zhuan-Yun,Sun, Wei-Xin,Wang, Jia-Zheng,Shen, Xiao-Ru,Zhan, Chao,Devasenathipathy, Rajkumar,Zhou, Jian-Zhang,Wu, De-Yin,Mao, Bing-Wei,Tian, Zhong-Qun
supporting information, p. 17489 - 17498 (2020/11/12)
An attractive field of plasmon-mediated chemical reactions (PMCRs) is developing rapidly, but there is still incomplete understanding of how to control the kinetics of such a reaction related to hot carriers. Here, we chose 8-bromoadenine (8BrAd) as a probe molecule of hot electrons to investigate the influence of the electrode potential, laser wavelength, and power on the PMCR kinetics on silver nanoparticle-modified silver electrodes. Plasmonic hot electron-mediated cleavage of the C-Br bond in 8BrAd has been investigated by combining in situ electrochemical surface-enhanced Raman spectroscopy and density functional theory calculations. The experimental and theoretical results reveal that the energy position of plasmon relaxation-generated hot electrons can be modulated conveniently by applied potentials and laser light. This allows the proposal of a mechanism of modulating the matching energy of the hot electron of plasmon relaxation to promote the efficiency of PMCRs in electrochemical interfaces. Our work will be helpful to design surface plasmon resonance photoelectrochemical reactions on metal electrode surfaces of nanostructures with higher efficiency.
Adenine intermediate pyrimidine-azo compound and preparation method thereof
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Paragraph 0023, (2017/07/14)
The invention relates to an adenine intermediate pyrimidine-azo compound and a preparation method thereof. The preparation method comprises the following steps of: 1) dissolving primary amine in mixed-acid solution, dripping sodium nitrite solution to prepare diazonium salt shown in a formula (3), adding malononitrile for dissolving, and dripping alkaline solution to regulate a pH value of reaction solution and generate coupling reaction, thereby obtaining an intermediate pyrimidine-azo compound (4); 2) adding the intermediate pyrimidine-azo compound (4) prepared in the step 1) into formamide, introducing liquid ammonia, and heating to carry out high-temperature condensation and cyclization reaction, thereby obtaining an adenine intermediate pyrimidine-azo compound (5), wherein a series of derivatives of the adenine intermediate pyrimidine-azo compound can be prepared by selecting different primary amines. The adenine intermediate pyrimidine-azo compound and the preparation method have the advantages that water is used as a solvent in the step 1), and the solvent used in the step 2) can be repeatedly used, so that the 'three wastes' are fewer, and the environment-friendly effect is achieved; and the cost is low, so that the industrialization is easy and the economic benefit is obvious.
Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins
Price, Neil P.J.,Furukawa, Takayuki,Cheng, Fang,Qi, Jianzhao,Chen, Wenqing,Crich, David
, p. 405 - 414 (2014/06/10)
Septacidins and spicamycins are acylated 4-aminoheptosyl-β-N- glycosides produced by Streptomyces fimbriatus and S. alanosinicus, respectively. Their structures are highly conserved, but differ in the stereochemistry of the 4-aminoheptosyl residues. The o
