Uracil and Thymine

CHEMICAL NAME = 4-Aminopyrimidin-2(lH)-one CAS NUMBER = 71-30-7 MOLECULAR FORMULA = ChLN,0 MOLAR MASS =111.1 g/mol 

CHEMICAL NAME = 5-Methylpyrimidine-2,4(lH,3H)-dione CAS NUMBER = 65-71-4 MOLECULAR FORMULA = CGHGN, 0, 

Cytosine, thymine, and uracil are pyrimidines along with adenine and guanine they account for the five nucleic acid bases. Pyrimidines are heterocyclic single-ringed compounds based on the structure of pyrimidine. Cytosine, thymine, and uracil, like adenine and guanine, form nucleosides and nucleotides in RNA and DNA. When the bases combine with ribose, a ribo-nucleoside forms and when it attaches to deoxyribose, a deoxyribosenucleoside is formed. Names of the nucleoside are summarized in Table 29.1. These in turn combine with phospho-ryl groups, in a process called phosphorylation, to form their respective nucleotides that form nucleic acids. The nucleotides can be tri, di, and mono phosphate nucleotides similar to the way in which adenine forms ATP, ADP, and AMP. 

Cytosine and thymine were first isolated by hydrolysis of calf thymus tissue by Albrecht Kossel (1853-1927) and A. Neumann during 1893-1894. Thymine s structure was published in 1900 and confirmed over the next several years when it was synthesized by several investigators. In 1903, cytosine was synthesized by Henry Lord Wheeler (1867-1914) and Treat B. Johnson, confirming its structure. Uracil was first isolated in 1900 from yeast nucleic acid found in bovine thymus and herring sperm. The methylation of uracil produces thymine thymine is also called 5-methyluracil because methylation takes place at the fifth carbon in uracil to produce thymine. 

000 and 100,000 genes contained in their 46 chromosomes, and the genetic code in humans consists of roughly 5 billion base pairs. 

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It is the parent substance of a group of compounds which includes cytosine, thymine and uracil, which are constituents of nucleic acids and barbituric acid and its derivatives, which are important medicinally. 

Pyrimidine and imidazole rings are particularly important in biological chemistry. Pyrimidine, for instance, is the parent ring system in cytosine, thymine, and uracil, three of the five heterocyclic amine bases found in nucleic acids An aromatic imidazole ring is present in histidine, one of the twenty amino acids found in proteins. 

Nucleotides can be linked together into oligonucleotides through a phosphate bridge at the 5 position of one ribose unit and the 3 position of another. The purine bases, adenine and guanine, have two heterocyclic rings, while the pyrimidines cytosine, thymine, and uracil have one. The structure of adenosine monophosphate is shown in Figure 11. 

A computational study was concerned with the effect of solvation on the radical ion involved in CDP photolyase enzyme-catalysed reversion of thymine and uracil cyclobutane dimers stimulated by visible light <06T6490>. 

Figure 1.43 indicates major sites of reactivity within the ring structures for nucleophilic displacement reactions. Cytosine, thymine, and uracil all react toward nucleophilic attack at the same two sites, the C-4 and C-6 positions. The presence of powerful nucleophiles, even at neutral pH, can lead to significant base modification or cleavage with pyrimidine residues (Debye, 1947). For instance, hydrazine spontaneously adds to the 5,6-double bond, initiating further ring reactions,... 

Other reactions characterized for pyrimidine residues include mercuration at C-5 of cytosine or uracil (Hopman et al., 1986), cycloaddition to the 5,6-double bond of thymine and uracil (Cimino et al., 1985), and thiolation at the C-4 amino group of cytosine (Malcom and Nicolas, 1984). 

As in the case of pyrimidine bases discussed previously, adenine and guanine are subject to nucleophilic displacement reactions at particular sites on their ring structures (Figure 1.50). Both compounds are reactive with nucleophiles at C-2, C-6, and C-8, with C-8 being the most common target for modification. However, the purines are much less reactive to nucleophiles than the pyrimidines. Hydrazine, hydroxylamine, and bisulfite—all important reactive species with cytosine, thymine, and uracil—are almost unreactive with guanine and adenine. 

The derivatives of poly-L-lysine having pendant nucleic acid bases, that is, adenine, thymine and uracil were prepared as shown in the following scheme ... 

The contents of the nucleic acid bases in the poly-L-lysine derivatives were determined by UV spectra of the polymers after hydrolysis The polymers were hydrolyzed in 6 N-hydrochloric acid at 105°C for 24 hr, into lysine dihydrochloride and the carboxyethyl derivatives of the nucleic acid bases. The quantitative calculation was made relative to the standard sample of the carboxyethyl derivative of the nucleic acid bases. The analytical data are listed in Table 1. It was found that the thymine and uracil derivatives was completely substituted to polylysine. Low value in case of adenine base in the polymer may be attributed to the unstability of the activated ester, Ade-PNP (2), and may also be explained in terms of the steric interaction among bulky pendant groups of the polymer. When the poly-L-lysine containing about 50 mol % adenine units was again treated with Ade-PNP, the adenine unit content in the polymer increased up to 74 mol %(,] ). 

Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nudeic add constituents (cytosine, thymine, and uracil) and form the basic structure of the barbiturates. [NIH]... 

There are two types of bases pyrimidines and purines (Fig. A2.5). The pyrimidine bases include cytosine, thymine, and uracil. Cytosine is found in... 

Ishihara, H. Photodimerization of thymine and uracil on filter paper, Photochem. Photobiol, 2 455-460, 1963. 

LCA toward amino acids and nucleic bases has also been measured. Wesdemiotis and Cerda measured the alkali metal ion affinities of nucleobases in the gas phase from the dissociation of metal ion-bound heterodimers [nucleobase + B]M+, in which B represents a reference base of known affinity and M is an alkali metal. By assessing the dimer decomposition for two different internal energies, entropy is deconvoluted from enthalpy and LCA values are obtained. For guanine, cytosine, adenine, thymine and uracil, the corresponding Li+-nucleobase bond energies are as follows 57.2, 55.5, 54.1,... 

Inaki (1992) synthesized a wide range of nucleobase-functionalized random and homopolymers. In addition, Inaki et al. (1980) synthesized block copolymers containing thymine and uracil groups in the main chain through ring-opening cationic and anionic polymerization of cychc derivatives of the nucleobases. 

Tautomeric structures of adenine, guanine, cytosine, thymine and uracil are—... 

Adsorption of adenine and coadsorption of adenine-thymine and uracil-thymine on Au(lll) has been reported [300]. Adenine was chemisorbed in two different states. Mutual interaction between adenine and thymine was detectable only at... 

Photolysis of a frozen mixture of 5 x 10 4M thymine-2-14C and 5 x 10" M uracil-2-14C gave a thymine dimer, a uracil dimer, and a mixed dimer of thymine and uracil,10,32 47 with the identities established as usual by the stability to heat and by photoreversion to monomers in solution. Wacker reports that the uracil dimer obtained in that investigation showed some instability to heat. These collected bits of evidence taken together with the reported441 thermal instability and chromatographic similarity of a synthetic tram dimer suggests that the dimer ordinarily obtained from uracil may be a mixture.46... 

The increase in absorbance at 240 nm upon saturation of the 5,6 double bond is considerably more pronounced for cytosine than for thymine and uracil. Thus the cross section of the cytosine dimer for monomerization at 240 nm is high, and the equilibrium concentration of dimer at various wavelengths is smaller for cytosine than for the other two pyrimidines.57... 

The Mg+ complexes of cytosine, thymine and uracil are the most complex system studied via photodissociation spectroscopy to date . A complication for these systems is that these nucleobases can exist in various tautomeric forms and that complexation of a metal can change the stability order of the tautomers. DFT calculations located four tautomeric Mg(cytosine)+ complexes, and three of these (29, 30, and 31) were suggested to be responsible for the four reactive photofragment ions 32-35 observed at a wavelength of 360 nm (Scheme 4) . Related photofragmentation reactions were observed for the Mg(thymine)+" and Mg(uracil)+" complexes . ... 

ROS can also deaminate 5-methylcytosine and cytosine to give thymine and uracil (Fig. 6.42). 

D models of Adenine, Guanine, Cytosine, Thymine, and Uracil... 

The pyrimidine base units cytosine, thymine, and uracil contain six-member nitrogenous ring structures with various points of unsaturation. Thymine and uracil are similar, containing the same double bond between carbons 5 and 6 and the same two ketone groups on C-2 and C-4 of the ring, but differ only in the presence of a methyl... 

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