Purine bases adenine

FIGURE 11.4 The common purine bases—adenine and guanine—in die tautomeric forms predominant at pH 7. 

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. 

Adenine phosphoribosyltransferase (APRT) deficiency is an inherited disorder of purine metabolism and is inherited in an autosomal recessive manner (K18, V7). This enzyme deficiency results in an inability to salvage the purine base adenine, which is oxidized via the 8-hydroxy intermediate by xanthine oxidase to 2,8-di-hydroxyadenine (2,8-DHA). This produces crystalluria and the possible formation of kidney stones due to the excretion of excessive amounts of this insoluble purine. Type I, with virtually undetectable enzyme activity, found predominantly in Caucasians, is found in homozygotes or compound heterozygotes for null alleles. Type II, with significant APRT activity, found only in Japan, is related to a missense mu-... 

Figure 11-4. Molecular orbitals for the purine bases adenine and guanine...

Shukla and coworkers have studied the excited states of purine bases, adenine and guanine, in water using CIS with the self-consistent reaction field (SCRF) to model the water [217,218], Tomasi and coworkers have also studied the purine bases... 

As A. and B. Pullman showed more than 40 years ago, the purine base adenine occupies a unique situation in the purine family in comparison to the other purines, it has the greatest resonance energy per -electron, i.e., it is more stable, and thus likely to have been incorporated preferentially into biomolecules (Pullman, 1972). 

This study again shows the prime importance of the purine base adenine, whether in the vastness of interstellar space or in the biochemical processes taking place in a single cell (Glaser et al 2007). 

The tautomerisation of the purine bases adenine and guanine and of the pyrimidine bases thymine, cytosine, and uracil has important implications in molecular biology, and the occurrence of rare tautomeric forms of these bases has been suggested as a possible cause of spontaneous mutagenesis (Lowdin, 1965 Pullman and Pullman, 1971 Kwiatowski and Pullman, 1975). Three of the most likely tautomers for cytosine are shown in [87]—[89], together with the less likely imino forms [90] and [91] (Scanlan and Hillier,... 

The transport of amino acids at the BBB differs depending on their chemical class and the dual function of some amino acids as nutrients and neurotransmitters. Essential large neutral amino acids are shuttled into the brain by facilitated transport via the large neutral amino acid transporter (LAT) system [29] and display rapid equilibration between plasma and brain concentrations on a minute time scale. The LAT-system at the BBB shows a much lower Km for its substrates compared to the analogous L-system of peripheral tissues and its mRNA is highly expressed in brain endothelial cells (100-fold abundance compared to other tissues). Cationic amino acids are taken up into the brain by a different facilitative transporter, designated as the y system, which is present on the luminal and abluminal endothelial membrane. In contrast, active Na -dependent transporters for small neutral amino acids (A-system ASC-system) and cationic amino acids (B° system), appear to be confined to the abluminal surface and may be involved in removal of amino acids from brain extracellular fluid [30]. Carrier-mediated BBB transport includes monocarboxylic acids (pyruvate), amines (choline), nucleosides (adenosine), purine bases (adenine), panthotenate, thiamine, and thyroid hormones (T3), with a representative substrate given in parentheses [31]. 

The bases that occur in nucleic acids are aromatic heterocyclic compounds derived from either pyrimidine or purine. Five of these bases are the main components of nucleic acids in all living creatures. The purine bases adenine (abbreviation Ade, not A ) and guanine (Gua) and the pyrimidine base cytosine (Cyt) are present in both RNA and DNA. In contrast, uracil (Ura) is only found in RNA. In DNA, uracil is replaced by thymine (Thy), the 5-methyl derivative of uracil. 5-methylcyto-sine also occurs in small amounts in the DNA of the higher animals. A large number of other modified bases occur in tRNA (see p. 82) and in other types of RNA. 

The nucleotides are among the most complex metabolites. Nucleotide biosynthesis is elaborate and requires a high energy input (see p. 188). Understandably, therefore, bases and nucleotides are not completely degraded, but instead mostly recycled. This is particularly true of the purine bases adenine and guanine. In the animal organism, some 90% of these bases are converted back into nucleoside monophosphates by linkage with phosphori-bosyl diphosphate (PRPP) (enzymes [1] and [2]). The proportion of pyrimidine bases that are recycled is much smaller. 

ATP Regarded as Store House of Energy Adenosine triphosphate (ATP) in a nucleotide consists of purine base adenine, a pentose sugar ribose and three molecules of phosphate. It contains two oxygen to phosphorus bonds between two phosphate units. These phosphorus bonds are called high energy phosphatic bonds. 

The sugar component in RNA is ribose, whereas in DNA it is 2-dexoyribose. In deoxyribonucleotides, the heterocyclic bases are purine bases, adenine and guanine, and pyrimidine bases, cytosine and thymine. In ribonucleotides, adenine, guanine and cytosine are present, but not thymine, which is replaced by uracil, another pyrimidine base. 

Both DNA and RNA contain two major purine bases, adenine (A) and guanine (G), and two major pyrimidines. In both DNA and RNA one of the pyrimidines is cytosine (C), but the second major pyrimidine is not the same in both it is thymine (T) in DNA and uracil (U) in RNA Only rarely does thymine occur in RNA or uracil in DNA The structures of the five major bases are shown in Figure 8-2, and the nomenclature of their corresponding nucleotides and nucleosides is summarized in Table 8-1. 

Both DNA and RNA contain the same purine bases adenine (A) and guanine (G). Both DNA and RNA contain the pyrimidine cytosine (C), but they differ in their second pyrimidine base DNA contains thymine (T), whereas RNA contains uracil (U). T and U differ by only one methyl group, which is present on T but absent on U (Figure 22.1). [Note Unusual bases are occasionally found in some species... 

The purine bases, adenine and guanine, participate in nature by providing structural elements of nucleic acids and numerous cofactors. The deaminated products of adenine and guanine do not participate in these coenzymic functions except in a relatively few instances. For example, the relative ineffectiveness of inosine monophosphate (IMP) vs. 

The purine derivatives caffeine, theobromine, and theophylline (Figure 6.135) are usually referred to as purine alkaloids. As alkaloids they have a limited distribution, but their origins are very closely linked with those of the purine bases adenine and guanine, fundamental components of nucleosides, nucleotides, and the nucleic acids. Caffeine, in the form of beverages such as tea, coffee, and cola is one of the most widely consumed and socially accepted natural stimulants. It is also used medicinally, but theophylline is... 

The purine bases adenine and guanine and the pyrimidine bases cytosine, thymine, and uracil are all heterocycles. They typically have strong 7uT UV absorption bands and, due to the lone electron pairs on the heteroatoms, have additional low lying nn transitions. Furthermore, for some bases Tier states are... 

As much of the terminology used in molecular biology may be unfamiliar to some readers, it is appropriate to define some of the vocabulary and this is given in an appendix to this chapter. There are two types of nucleic acids, the ribonucleic acids (RNA) and the deoxyribonucleic acids (DNA). Genetic information is carried in the linear sequence of nucleotides in DNA. Each molecule of DNA contains two complementary strands of deoxyribonucleotides which contain the purine bases, adenine and guanine and the pyrimidines, cytosine and thymine. RNA is single-stranded, being composed of a linear sequence of ribonucleotides the bases are the same as in DNA with the exception that thymine is replaced by the closely related base uracil. DNA replication occurs by the polymerisation of a new complementary strand on to each of the old strands. 

Fig. 9.5 The molecular structures of DNA and RNA components the purine bases adenine and guanine, the pyrimidine bases cytosine, thymine and uracil and the structure of riboso-monophosphates.

The natural purine bases adenine and guanine do not show appreciable fluorescence under neutral conditions at room temperature. It was also found that purine itself shows only very low fluorescence intensity as a neutral molecule, but this increases markedly on either acid or alkaline titration. For the purine monocation, emission at 400 nm with a quantum yield (4>f) of 0.008 was observed for the anion emission at 370 nm with of 0.045 was found. Appreciable fluorescence at room temperature can be observed for the adenine cation (Table 16), while, similarly, guanine in neutral solution is also nonfluorescent but emission becomes appreciable on protonation. However, with an increase of the pH beyond 11, decreased fluorescence is observed. A case where the neutral molecule is more fluorescent than either the cation or the anion is presented by purin-2-amine or purine-2,6-diamine as well as their nucleosides (Table 16, 5-7). 

Free purine bases, derived from the turnover of nucleotides or from the diet, can be attached to PRPP to form purine nucleoside monophosphates, in a reaction analogous to the formation of orotidylate. Two salvage enzymes with different specificities recover purine bases. Adenine phosphorihosyltransferase catalyzes the formation of adenylate... 

The bases found in nucleic acids are shown in Figure 28-17. Each type of nucleic acid contains two pyrimidine bases and two purine bases. The two purine bases adenine (A) and guanine (G) and the pyrimidine base cytosine (C) are found in both RNA and DNA. 

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