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Biochemistry Chemistry of Nucleic Acids

Nitrogenous Bases and Nucleosides

Topic overview

Start with the big picture

The five common nitrogenous bases fall into two structural groups: purines, with fused imidazole and pyrimidine rings, and pyrimidines, with a single six-membered ring. Their planar, aromatic structures support interactions such as π–π stacking. Tautomeric forms can affect base pairing, while the predominant physiological forms are keto for guanine, thymine, and uracil, and amino for adenine and cytosine. Bases also absorb ultraviolet light at 260 nm. A nucleoside forms when a base links to a pentose sugar through a β-N-glycosidic bond. The sugar type distinguishes ribonucleosides from deoxyribonucleosides, and conformational features influence nucleic-acid structure. Nucleoside analogs use base or sugar mimicry in efforts to inhibit viral or cancer DNA synthesis.

Learning objectives

What you'll learn

  • Classify the common nitrogenous bases as purines or pyrimidines.
  • Relate ring structure, planarity, and tautomerism to base behavior.
  • Describe how a nitrogenous base and pentose sugar form a nucleoside.
  • Distinguish ribonucleoside and deoxyribonucleoside naming and structure.
  • Explain the relevance of nucleoside analogs to DNA synthesis inhibition.
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