Chapter 4: Nucleic Acids

Introduction to Nucleic Acids

Nucleic acids are essential biopolymers that store and transmit genetic information in all living organisms. The two main types are DNA (deoxyribonucleic acid) and RNA (ribonucleic acid). Both are polymers composed of repeating nucleotide units.

Nucleotides: The Building Blocks of Nucleic Acids

Components of Nucleotides

Each nucleotide consists of three main components:

• Nitrogenous Base: Either a purine or pyrimidine.

• Pentose Sugar: Either ribose (in RNA) or deoxyribose (in DNA).

• Phosphate Group: Usually attached to the 5' carbon of the sugar.

The general structure can be represented as:

• Base (attached to 1' carbon of sugar)

• Sugar (ribose or deoxyribose)

• Phosphate (attached to 5' carbon, can be hydrolyzed to form di- or triphosphates)

Example: Adenosine monophosphate (AMP) contains adenine (base), ribose (sugar), and one phosphate group.

Nitrogenous Bases

Classification and Structure

Nitrogenous bases are aromatic heterocyclic molecules. They are classified by their ring structure:

• Purines: Double-ring structures. Examples: Adenine and Guanine.

• Pyrimidines: Single-ring structures. Examples: Cytosine, Thymine (DNA), and Uracil (RNA).

The base is always attached to the 1' carbon of the pentose sugar via a glycosidic bond.

Purines

• Adenine (A): Found in both DNA and RNA.

• Guanine (G): Found in both DNA and RNA.

Pyrimidines

• Cytosine (C): Found in both DNA and RNA.

• Thymine (T): Found only in DNA.

• Uracil (U): Found only in RNA.

Example: The difference between thymine and uracil is the presence of a methyl group in thymine.

Properties of Nucleotide Bases

• Bases can exist in different tautomeric forms (e.g., keto/enol, amino/imino), which can affect hydrogen bonding and base pairing.

• These tautomeric shifts are rare but can lead to mutations during DNA replication.

Nucleosides and Nucleotides

Nucleosides

A nucleoside consists of a nitrogenous base linked to a pentose sugar (no phosphate group).

• RNA nucleosides contain ribose.

• DNA nucleosides contain deoxyribose (lacking a 2' hydroxyl group).

Example: Adenosine is a nucleoside composed of adenine and ribose.

Nucleotides

A nucleotide is a nucleoside with one or more phosphate groups attached, typically at the 5' position of the sugar.

• Nucleotides are the monomeric units of DNA and RNA.

• Phosphate groups can also attach at other hydroxyl positions (e.g., 3').

Example: Guanosine diphosphate (GDP) contains guanine, ribose, and two phosphate groups.

The DNA Double Helix

Structural Organization

DNA is organized as a double helix, with two strands winding around a common axis in a right-handed fashion. The bases occupy the core, while the sugar-phosphate backbone is on the outside.

• Base pairs are stacked with a 36° angle between each, resulting in 10 base pairs per turn (360°).

• Hydrogen bonding between complementary bases stabilizes the helix.

Example: The classic B-form DNA has a major and minor groove, which are important for protein-DNA interactions.

Base Pairing

• Adenine (A) pairs with Thymine (T) via two hydrogen bonds.

• Guanine (G) pairs with Cytosine (C) via three hydrogen bonds.

This specific pairing is known as Watson-Crick base pairing and is fundamental to the fidelity of genetic information.

Summary Table: Nucleic Acid Components

Key Equations

• Base Pairing Rule: and in double-stranded DNA.

• Total Purines = Total Pyrimidines:

Additional info:

• The aromaticity and tautomeric forms of bases contribute to the chemical stability and mutagenic potential of nucleic acids.

• Base stacking and hydrophobic interactions further stabilize the double helix structure.