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Chapter 4 Nucleic Acids, Sections 4.1-4.3

Nucleic Acids

Introduction to Nucleic Acids

  • Definition: Nucleic Acids (NAs) are polymers of nucleotides.

  • Components of a Nucleotide: Each nucleotide is comprised of three primary components:

    1. Base: An aromatic heterocyclic molecule, either a Purine or a Pyrimidine.

    2. Sugar Molecule: A pentose sugar, specifically Deoxyribose (in DNA) or Ribose (in RNA).

    3. Phosphate Group: Typically attached to the 5' carbon of the sugar, but can be attached at other hydroxyl positions (e.g., 2', 3').

    • The base and phosphate group are generally positioned above the plane of the sugar.

Bases: Purines and Pyrimidines

  • Nature: Bases are aromatic, heterocyclic molecules that vary between different nucleotides.

  • Primary Classes based on Ring Structure:

    1. Purines: Consist of a fused five-membered and six-membered ring system (e.g., Adenine (A), Guanine (G)).

    2. Pyrimidines: Consist of a single six-membered ring system (e.g., Cytosine (C), Uracil (U) in RNA, Thymine (T) in DNA).

  • Structural Characteristics:

    • Despite their aromaticity, the rings are not perfectly flat due to exocyclic groups.

    • They are still considered fully aromatic.

  • Tautomerization: Purine and pyrimidine bases can exist in different tautomeric forms, primarily Keto-Enol and Amino-Imino tautomerism. This property is crucial for hydrogen bonding within nucleic acids.

Nucleosides

  • Definition: A nucleoside consists of a base covalently linked to a pentose sugar.

  • Two Classes in Nature:

    • Ribonucleosides: Contain Ribose as the sugar, found in RNA.

    • Deoxyribonucleosides: Contain Deoxyribose as the sugar, found in DNA. Deoxyribose is distinguished by the absence of a hydroxyl group at the 2' carbon position.

Nucleotides: The Monomer Units

  • Definition: A nucleotide is a nucleoside with one or more phosphate groups attached.

  • Role: Nucleotides are the fundamental monomer units that polymerize to form DNA and RNA.

  • Phosphate Attachment:

    • Most Common Position: The phosphate group is most frequently attached at the 5' position of the pentose sugar in both RNA and DNA.

    • Alternative Positions: Phosphate groups can attach to any available hydroxyl group of the sugar (e.g., 2', 3', 5') depending on the context.

  • Phosphorylation State: Nucleotides can be mono-, di-, or tri-phosphorylated (e.g., AMP, ADP, ATP).

  • Nomenclature: By default, a 5'-phosphate is assumed unless explicitly stated otherwise in the nucleotide name (e.g., Adenosine monophosphate typically refers to Adenosine 5'-monophosphate).

    • Knowing the name should allow one to derive the structure (e.g., Adenosine 2'-monophosphate, Adenosine 3'-monophosphate, Adenosine 5'-monophosphate, or cyclic AMP).

Nucleic Acid Polymerization: Phosphodiester Linkages

  • Process: Nucleic acids are synthesized by linking individual nucleotides (also called