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Biology · Ch 9 — Biomolecules

Nucleic Acids: Structure of DNA and RNA

9.7

Nucleic Acids: Structure of DNA and RNA

Nucleic acids are the biomacromolecules responsible for storing, transmitting and expressing genetic information in every living cell, and are themselves polymers built from repeating monomer units called nucleotides.

Each nucleotide is composed of three distinct chemical parts: a nitrogenous base, a five-carbon (pentose) sugar, and one or more phosphate groups. The nitrogenous bases fall into two chemical categories -- the purines, adenine and guanine, built around a fused double-ring structure, and the pyrimidines, cytosine, thymine and uracil, built around a single ring. When a nitrogenous base is joined to the pentose sugar alone, without any phosphate group, the resulting unit is called a nucleoside; the addition of one or more phosphate groups to a nucleoside produces a nucleotide, and it is nucleotides, joined one to the next through phosphodiester bonds between the phosphate of one unit and the sugar of the next, that form the long backbone of a nucleic acid chain.

The two classes of nucleic acid are distinguished chiefly by their sugar and by one of their four bases. DNA (deoxyribonucleic acid) contains the sugar deoxyribose, which lacks a hydroxyl group at its 2' carbon, and uses the base thymine in place of uracil; its four bases are adenine, guanine, cytosine and thymine. RNA (ribonucleic acid) contains the sugar ribose, retaining the 2' hydroxyl group, and uses uracil in place of thymine; its four bases are adenine, guanine, cytosine and uracil.

The three-dimensional structure of DNA was resolved by James Watson and Francis Crick in 1953, building on the X-ray diffraction data of Rosalind Franklin and Maurice Wilkins, as a double helix: two polynucleotide strands, running in opposite (antiparallel) directions, wound around a common central axis in a right-handed coil, with roughly ten base pairs per complete turn. The sugar-phosphate backbones of the two strands lie on the outside of the helix, while the nitrogenous bases project inward and pair with one another according to a strict rule of complementary base pairing -- adenine always pairs with thymine through two hydrogen bonds, and guanine always pairs with cytosine through three hydrogen bonds -- so that the sequence of bases on one strand precisely dictates the sequence on the other, providing the structural basis for both the storage and the accurate copying of genetic information. …

Table 9.7DNA versus RNA

Feature | DNA | RNA

Pentose sugar | Deoxyribose | Ribose

Pyrimidine base | Thymine (with adenine, guanine, cytosine) | Uracil (with adenine, guanine, cytosine)

Strands | Usually double-stranded | Usually single-stranded

Overall shape | Right-handed double helix | Linear strand, often folded into loops …

Figure 9.7The Watson-Crick DNA Double Helix

What this figure shows. A schematic diagram of a short stretch of double-stranded DNA drawn as two parallel ribbons twisting around a common vertical axis to form a right-handed double helix, winding so that roughly ten base pairs are shown per complete turn. Short horizontal rungs connect the two ribbons at regular intervals, each rung representing one base pair: rungs labelled A-T are drawn with two short parallel dashed lines between the bases (representing two hydrogen bonds), and rungs labelled G-C are drawn with three short parallel dashed lines (representing three hydrogen bonds). Small alternating pentagon and circle shapes along each outer ribbon represent the alternating deoxyribose sugar and phosphate groups making up the sugar-phosphate backbone, running in opposite directions on the two strands as indicated by smal …