C-Adenine

The DNA base pairs guanine (G), cytosine (C), adenine (A) and thymine (T). The uracil-2,6-diaminopyridine pair can also form three hydrogen bonds but has a much lower association constant than G-C. 

Figure 1 Free radical structures, parent compounds, and stable end products for the various components of DNA (a) deoxyribose, (b) guanine, (c) adenine, (d) thymine, and (e) cytosine. Panel (f) shows trapping of the electron and hole by proton transfer in the GC base pair in duplex DNA.

The close correspondence of the DNA absorption spectrum with that of a mixture of mononucleotides of the same composition illustrates the weak nature of the interactions between neighboring purine and pyrimidine bases guanine (G), cytosine (C), adenine (A), and thymine (T) at an interplanar separation of 3.36 A in the unexcited double-helical configuration. On the other hand the structureless fluorescence band of (calf-thymus) DNA is red-shifted by 3500 cm-1 from the fluorescence spectral origin of the mononucleotides it closely resembles the fluorescence spectrum of the dinocleotide ApT (and of poly dAT) and is accordingly identified131 with the fluorescence... 

Fig. 26. Nucleic acid structures. A The structure of the four bases in DNA, guanine (G), cytosine (C) adenine (A) and thymine (T). Uracil (U) replaces thymine (T) in RNA. B The spontaneous attraction of A for T and C for G allows the recognition of homologous sequences in aqueous solutions and the strong and specific hybridization of one sequence with its homologous sequence. C DNA forms a double helix at body temperature, which can be denatured to separate the strands by heating. D single stranded mRNA structure.

The basic monomers of nucleic acids are nucleotides which are made up of heterocyclic nitrogen-containing compounds, purines and pyrimidines, linked to pentose sugars. There are two types of nucleic acids and these can be distinguished on the basis of the sugar moiety of the molecule, Ribonucleic acids (RNA) contain ribose, while deoxyribonucleic acid (DNA) contains deoxyribose. The bases cytosine (C) adenine (A) and guanine (G) are common in both RNA and DNA. However, RNA molecules contain a unique base, uracil (U), while the unique DNA base is thymidine (T). These differences in the base structure markedly affect the secondary structures of these polymers. The structures of DNA and RNA are outlined in Appendix 5.2. 

Bases In DNA there are four bases adenine (abbreviated A), guanine (G), thymine (T) and cytosine (C). Adenine and guanine are purines thymine and cytosine are pyrimidines. 

The bases found in RNA (ribonucleic acid) are the purine heterocyclics adenine (6-aminopurine) and guanine (2-amino-6-oxypurine) and their complementary pyrimidine bases uracil (2,4-dioxypyrimidine) and cytosine (2-oxy-4-aminopyrimidine), respectively (Section 1, Appendix). In RNA double-stranded duplexes adenine (A) base-pairs with uracil (U) via two hydrogen bonds (A=U) and guanine base-pairs with cytosine (C) via 3 hydrogen bonds (G=C). Adenine forms the nucleoside adenosine by an N-glycosidic link with the... 

Figure 3 Supramolecular dimers, trimers, and oligomers generated by H-bonding self-assembly of (a) adenine, (b) uracil, and (c) adenine-uracil base-pair. (R = sugar, alkyl, etc.)...

A sample of labeled RNA containing C -adenine and H -uracil yielded... 

Just how is the structure of nucleic acids related to their function in heredity Nucleic acids control heredity on the molecular level. The double helix of DNA is the repository of the hereditary information of the organism. The information is stored as the sequence of bases along the polynucleotide chain it is a message written in a language that has only four letters, A, G, T, C (adenine, guanine, thymine, cytosine). 

Thymine (T) Cytosine (C) Adenine (A) Guanine 5-Hydroxymethyl-uracil (HMU) 6-Methylamino-purine (HMA)... 

Amidation of 2,5-anhydro-D-allonic acid (106) with 4,5,6-triaminopyri-midine (506) gave the corresponding amide 507, which then thermally cyclodehydrated to 7-amino-2-j8-D-ribofuranosylimidazo[4,5-d]pyrimidine (8-)8-D-ribofuranosyladenine or C-adenine) (508) (69CCC247) (Scheme 137). 

All nncleic acids are polynucleotides, with each nucleotide being made np of a base, a sugar unit, and a phosphate. The composition of DNA differs from that of RNA in two major ways (see Figure 1). Whereas DNA contains the bases gnanine (G), cytosine (C), adenine (A), and thymine (T), RNA contains G, C, and A, but it contains uracil (U) in place of thymine. Both DNA and RNA contain a five-membered cyclic sngar (a pentose). RNA contains a ribose sngar. The sugar in DNA, however, is 2 -deoxyribose. 

Numerous syntheses have also been reported for arabinofuranosyl nucleoside analogues, prepared either conventionally from arabinofuranosyl derivatives or via 2,2-anhydro-nucleosides obtained from appropriate ribonucleosides. 5-Aza-cytosine-D-arabinoside has been synthesized and found to show similar antiviral activity to Ara-C(arabinosyl-cytosine). 7-a-, 7-<3-, 9-0 -, and 9- 3-arabino-furanosyl derivatives of 3-deazaguanine have also been prepared, but none showed any anti-tumour activity. 9-(o -D-Arabinofuranosyl)-8-aza[2- C]-adenine, 7-(/3-D-arabinofuranosyl)-pyrrolo[2,3-d]pyrimidine-4(3//)-one (15)," l-(a-D-arabinofuranosyl)- and l-(/3-D-xylofuranosyl)-4-nitropyrazole, and Ot-arabino-nucleosides of 5-fluoro-cytosine and -uracil derivatives have also been prepared. An improved synthesis of 9-(/3-D-arabinofuranosyl)-2-fluoro-adenine has been reported. The ratio of o to 3 anomers obtained by phase-transfer reaction of 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide with 6-chloro-2-thiomethyl-7-deazapurine varied with the quaternary ammonium salt used as a catalyst, although the jU-anomer predominated in every case. 2,2-Anhydro-nucleosides have been used to prepare l-j3-D-arabinofiiranosyl derivatives of 5-alkylthio-uracils, 5-ethyl-cytosine, and 5-ethyl-uracil, 8-alkylamino-purines, and 2-aralkylamino-l,4-dihydro-4-imino-pyrimidine hydrochlorides (16). ... 

The example just reported is of immense importance because it pertains to guanine (G), cytosine (C), adenine (A), and thymine (T). Thanks to these two pairs of synthons (GC and AT), we exist, because the G, C, A, and T represent the four letters that are sufficient to write the book of life, word by word, in a single molecule of DNA. The words, the sentences, and the chapters of this book decide the majority of the veiy essence of your (and my) personality. The whole DNA strand may be considered as a large single synthon. The synthon has its important counterpart which fits the DNA perfectly because of the complementarity. The molecular machine that synthesizes this counterpart molecule (a negative ) is the polymerase, a wonderful molecule (that you will learn more about in Chapter 15). Any error in this complementarity results in a mutation. ... 

The three pyrimidine bases are uracil, thymine, and cytosine, usually abbreviated U, T, and C. Adenine (A) and guanine (G) are the two purine bases. Adenine, guanine, and cytosine are found in both DNA and RNA, but uracil is ordinarily found only in RNA, and thymine only in DNA. Structural formulas of the five bases are given in I Figure 11.3. 

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