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:
Base: An aromatic heterocyclic molecule, either a Purine or a Pyrimidine.
Sugar Molecule: A pentose sugar, specifically Deoxyribose (in DNA) or Ribose (in RNA).
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:
Purines: Consist of a fused five-membered and six-membered ring system (e.g., Adenine (A), Guanine (G)).
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