65-71-4 Usage
Thymine
Thymine, also known as 5-methyl uracil, the earliest isolated from calf thymus and then got the name, and is the major pyrimidine component of deoxyribonucleic acid. And it can be linked with deoxyribose through the glycoside chain to form deoxythymidine, the triphosphate of deoxythymidine triphosphate, the triphosphoric acid of which can compound to deoxythymidine triphosphate, which is a precursor of thymine during deoxyribonucleic acid biosynthesis.
Figure 1 the structure of thymine.
Physiological function
Nucleotides consist of bases, pentoses and phosphates, and constitute the basic unit of biological macromolecular nucleic acid. According to the difference of pentose in nucleotide composition, nucleotides can be divided into ribonucleotides and deoxyribonucleotides, and there constitute the two types of nucleic acids: ribonucleic acid (RNA) and deoxyribonucleic acid (DNA). The Compositions of nucleotide base are two categories, pyrimidine and purine. Pyrimidine is a 6-membered heterocyclic organic compound containing two nitrogen atoms. Common pyrimidine bases in nucleotides are cytosine (C), uracil (V) and thymine (T). Purine is a heterocyclic compound with four-nitrogen. Adenine (A) and bird purine (G) are the major purine bases that make up the nucleotides.Purine and pyrimidine are heterocyclic nitrogen-containing compounds that are necessary for biological (including human) nucleic acid metabolism. Purine, pyrimidine and ribose and phosphate combine to form RNA; purine, pyrimidine and deoxyribose and phosphate combine to produce DNA.DNA is the main chemical constituent of genes, which plays an important role in the transmission of genes, and the main function of RNA is the regulation of intracellular protein synthesis. the final metabolism product of Purine is mainly uric acid. The clinically relevant purines are adenine and guanine. Important pyrimidines are thymine, cytosine and uracil. In the purine and pyrimidine metabolism must have all kinds of enzymes involved in to make the metabolic process according to normal procedure, the lack of any kind of these enzymes can cause the corresponding purine or pyrimidine metabolic disorders, resulting in clinical-specific symptoms such as whey aciduria Xanthineuria and Lesch-Nyhan syndrome. Others, such as primary children with gout; uraemia with partial phosphoribosyl transferase deficiency; female intelligence retardation, mutations and hyperuricemia syndrome; 2,8-dehydroadenurine and deaminase deficiency in children is rare.
This information was edited by lookchem Xiao Nan (2015-08-03).
The Four DNA Bases
There are four bases that support the formation of DNA. They are thymine, adenine, guanine, and cytosine and are also known by the acronyms T, A, G, and C. These bases are attracted to one another and form specific partnerships to help in the creation of DNA. DNA is a small molecule found in every cell of your body and is responsible for writing your body's genetic information.
DNA is best visualized by picturing a long, twisted, spiraling ladder. The inner portion of the ladder is constructed of rungs. If you picture the four bases of DNA as rungs that assist with the formation of the ladder, you can get a solid understanding of how the bases hold the DNA structure together. Just as the rungs have a responsibility to stabilize the ladder, the bases have a responsibility to stabilize the structure of DNA.
Thymine is an interesting base because it is the only one of the four bases found exclusively inside of DNA. The other bases are also found in RNA, which is often thought of DNA's cousin because of the close relationship and joint assistance the two often share genetic information transfer process.
Chemical properties
White crystalline powder, insoluble in water at room temperature, slightly soluble in alcohol, soluble in alkali, acid, formamide, DMF and pyridine. Melting point is 320-330 ° C.
Uses
Different sources of media describe the Uses of 65-71-4 differently. You can refer to the following data:
1. (1) Thymine, along with adenine, guanine, and cytosine, is one of the four nucleic acid bases in DNA; thymine can be used to study chemical processes that affect DNA structure, such as a radiation-induced free radical product resulting in base cross-linking reaction and derivatization reaction. Thymine can be used to study the energy and hydrogen bonding kinetic parameters with other nucleic acid bases such as adenine; thymine is used for the development of (Hg) detectors with sensitive, nanoparticle-based structures and coordination chemistry.
(2) 5-methyl pyrimidine is an important component of genetic material, is the key intermediates of synthestising anti-AIDS drugs AZT, DDT and related drugs key intermediates, but also the starting material of synthetising anti-tumor, antiviral drug β-thymidine.
2. Thymine is a nitrogenous base component in the nucleic acid of DNA.
3. A nucleobase found in deoxyribonucleic acids (DNA).
4. Thymine (Zidovudine EP Impurity C) is a nitrogenous base component in the nucleic acid of DNA.
Chemical Properties
White, crystalline powder. Slightly soluble in hot water; insoluble
in coldwater, alcohol; sparingly soluble in ether;
readily soluble in alkalies.
Definition
Different sources of media describe the Definition of 65-71-4 differently. You can refer to the following data:
1. A nitrogenous
base found in DNA. It has a PYRIMIDINE
ring structure.
2. thymine: A pyrimidine derivativeand one of the major componentbases of nucleotides and the nucleicacid DNA.
3. ChEBI: A pyrimidine nucleobase that is uracil in which the hydrogen at position 5 is replaced by a methyl group.
Synthesis Reference(s)
The Journal of Organic Chemistry, 25, p. 149, 1960 DOI: 10.1021/jo01071a612
General Description
Thymine (Zidovudine Related Compound C) is a process related impurity of antiretroviral drug zidovudine. Zidovudine belongs to the class of drugs known as nucleoside reverse transcriptase inhibitors and is generally used in the prevention and treatment of HIV/AIDS.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Biochem/physiol Actions
Thymine used in studying DNA structure byirradtaion methods leading to cross-linking reactions and derivitizations. Thymine dimers are indicative of DNA damage. Thymine is used with metal (mercury) to form thymine?HgII?thymine (T?HgII?T) duplexes. Thymine starvation in bacteria leads to halt in DNA synthesis and is referred as thymine-less death.
Purification Methods
Crystallise thymine from EtOAc, 10% aqueous EtOH or water. It has m 318-320o after sublimation at 200o/12mm. Purify it by preparative (2mm thick) TLC plates of silica gel, eluting with ethyl acetate/isopropanol/water (75:16:9, v/v; RF 0.75). The desired spot is localated with a uv lamp, cut the band from the plate, place it in MeOH, shake and filter it through a millipore filter, then evaporate. [Infante et al. J Chem Soc, Faraday Trans 1 68 1586 1973, Beilstein 24 H 353, 24 I 330, 24 II 183, 24 III/IV 1292.]
Check Digit Verification of cas no
The CAS Registry Mumber 65-71-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 65-71:
(4*6)+(3*5)+(2*7)+(1*1)=54
54 % 10 = 4
So 65-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)
65-71-4Relevant articles and documents
Photoinduced deoxyribose C2′ oxidation in DNA. Alkali-dependent cleavage of erythrose-containing sites via a retroaldol reaction
Sugiyama, Hiroshi,Tsutsumi, Yasushi,Fujimoto, Kenzo,Saito, Isao
, p. 4443 - 4448 (1993)
Photoreactions of various 5-iodouracil- (1U)-containing oligonucleotides have been investigated. It was found that d(GCA1UGC)2 undergoes a competitive Cl′ and C2′ oxidation at the 5′ side of the 1U residue to give deoxyribonolactone-containing hexamer 1 and erythrose-containing hexamer 2, respectively. Upon heating under alkaline conditions, erythrose-containing hexamer 2 was shown to undergo a remarkably facile retroaldol reaction to give two fragments, both having phosphoroglycoaldehyde termini in high yields. On the basis of the chemical reactivity of 2, a new specific method for detection of the erythrose-containing sites resulting from deoxyribose C2′ oxidation in DNA was devised. Erythrose-containing sites were prepared by photoirradiation of duplex 1U-containing 13 mer 5′-d(CG1UGT'UTA1UAC 1UG)-3′/5′-d(CAGTATAAACACG)-3′. After photoirradiation, the reaction mixture was treated with hot alkali and NaBH4 and then subjected to enzymatic digestion. HPLC analysis of the digested mixture revealed the formation of modified mononucleotides 25-28, allowing the quantification of the erythrose-containing sites being produced at the 5′ side of all four 1U residues of the 13 mer. These results indicate that this method can be used for the detection and quantification of erythrose-containing sites resulting from deoxyribose C2′ oxidation in DNA.
The Peculiar Case of the Hyper-thermostable Pyrimidine Nucleoside Phosphorylase from Thermus thermophilus**
Kaspar, Felix,Neubauer, Peter,Kurreck, Anke
, p. 1385 - 1390 (2021/01/29)
The poor solubility of many nucleosides and nucleobases in aqueous solution demands harsh reaction conditions (base, heat, cosolvent) in nucleoside phosphorylase-catalyzed processes to facilitate substrate loading beyond the low millimolar range. This, in turn, requires enzymes that can withstand these conditions. Herein, we report that the pyrimidine nucleoside phosphorylase from Thermus thermophilus is active over an exceptionally broad pH (4–10), temperature (up to 100 °C) and cosolvent space (up to 80 % (v/v) nonaqueous medium), and displays tremendous stability under harsh reaction conditions with predicted total turnover numbers of more than 106 for various pyrimidine nucleosides. However, its use as a biocatalyst for preparative applications is critically limited due to its inhibition by nucleobases at low concentrations, which is unprecedented among nonspecific pyrimidine nucleoside phosphorylases.
Efficient biocatalytic synthesis of dihalogenated purine nucleoside analogues applying thermodynamic calculations
Giessmann, Robert T.,Kaspar, Felix,Klare, Hendrik F. T.,Kurreck, Jens,Neubauer, Peter,Paulick, Katharina,R?hrs, Viola,Wagner, Anke,Westarp, Sarah,Yehia, Heba
, (2020/02/28)
The enzymatic synthesis of nucleoside analogues has been shown to be a sustainable and efficient alternative to chemical synthesis routes. In this study, dihalogenated nucleoside analogues were produced by thermostable nucleoside phosphorylases in transglycosylation reactions using uridine or thymidine as sugar donors. Prior to the enzymatic process, ideal maximum product yields were calculated after the determination of equilibrium constants through monitoring the equilibrium conversion in analytical-scale reactions. Equilibrium constants for dihalogenated nucleosides were comparable to known purine nucleosides, ranging between 0.071 and 0.081. To achieve 90% product yield in the enzymatic process, an approximately five-fold excess of sugar donor was needed. Nucleoside analogues were purified by semi-preparative HPLC, and yields of purified product were approximately 50% for all target compounds. To evaluate the impact of halogen atoms in positions 2 and 6 on the antiproliferative activity in leukemic cell lines, the cytotoxic potential of dihalogenated nucleoside analogues was studied in the leukemic cell line HL-60. Interestingly, the inhibition of HL-60 cells with dihalogenated nucleoside analogues was substantially lower than with monohalogenated cladribine, which is known to show high antiproliferative activity. Taken together, we demonstrate that thermodynamic calculations and small-scale experiments can be used to produce nucleoside analogues with high yields and purity on larger scales. The procedure can be used for the generation of new libraries of nucleoside analogues for screening experiments or to replace the chemical synthesis routes of marketed nucleoside drugs by enzymatic processes.
Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases
Artsemyeva, Julia N.,Buravskaya, Tatiana N.,Esipov, Roman S.,Konstantinova, Irina D.,Litvinko, Natalia M.,Mikhailopulo, Igor A.,Miroshnikov, Anatoly I.,Remeeva, Ekaterina A.
, p. 2607 - 2622 (2020/11/26)
In the present work, we suggested anion exchange resins in the phosphate form as a source of phosphate, one of the substrates of the phosphorolysis of uridine, thymidine, and 1-(β-D-arabinofuranosyl)uracil (Ara-U) catalyzed by recombinant E. coli uridine (UP) and thymidine (TP) phosphorylases. α-D-Pentofuranose-1-phosphates (PF-1Pis) obtained by phosphorolysis were used in the enzymatic synthesis of nucleosides. It was found that phosphorolysis of uridine, thymidine, and Ara-U in the presence of Dowex 1X8 (phosphate; Dowex-nPi) proceeded smoothly in the presence of magnesium cations in water at 20-50 °C for 54-96 h giving rise to quantitative formation of the corresponding pyrimidine bases and PF-1Pis. The resulting PF-1Pis can be used in three routes: (1) preparation of barium salts of PF-1Pis, (2) synthesis of nucleosides by reacting the crude PF-1Pi with an heterocyclic base, and (3) synthesis of nucleosides by reacting the ionically bound PF-1Pi to the resin with an heterocyclic base. These three approaches were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52-93%).
