NUCLEIC ACIDS

NUCLEOTIDES AND NUCLEIC ACIDS

Nucleic acids are molecules that allow organisms to transfer genetic information from one
generation to the next. These macromolecules store the genetic information that determines
traits and makes protein synthesis possible.
Two examples of nucleic acids include: deoxyribonucleic acid (better known as DNA) and
ribonucleic acid (better known as RNA). These molecules are composed of long strands of
nucleotides held together by covalent bonds. Nucleic acids can be found within the nucleus
and cytoplasm of our cells.

Nucleic Acid Monomers

Nucleotides are composed of a nitrogenous base, a five-carbon sugar, and a phosphate group

Nucleic acids are composed of nucleotide monomers linked together. Nucleotides have three
parts:

• A Nitrogenous Base
• A Five-Carbon (Pentose) Sugar
• A Phosphate Group

Nitrogenous bases include purine molecules (adenine and guanine) and pyrimidine molecules
(cytosine, thymine, and uracil). In DNA, the five-carbon sugar is deoxyribose, while ribose is
the pentose sugar in RNA. Nucleotides are linked together to form polynucleotide chains.
They are joined to one another by covalent bonds between the phosphate of one and the sugar
of another. These linkages are called phosphodiester linkages. Phosphodiester linkages form
the sugar-phosphate backbone of both DNA and RNA.
Similar to what happens with protein and carbohydrate monomers, nucleotides are linked
together through dehydration synthesis. In nucleic acid dehydration synthesis, nitrogenous
bases are joined together and a water molecule is lost in the process. Interestingly, some
nucleotides perform important cellular functions as "individual" molecules, the most common
example being ATP.

DNA Structure

DNA is composed of a phosphate-deoxyribose sugar backbone and the four nitrogenous

bases: adenine (A), guanine (G), cytosine (C), and thymine (T)

DNA is the cellular molecule that contains instructions for the performance of all cell
functions. When a cell divides, its DNA is copied and passed from one cell generation to the
next generation. DNA is organized into chromosomes and found within the nucleus of our
cells. It contains the "programmatic instructions" for cellular activities. When organisms
produce offspring, these instructions in are passed down through DNA.

DNA commonly exists as a double stranded molecule with a twisted double helix shape.
DNA is composed of a phosphate-deoxyribose sugar backbone and the four nitrogenous
bases: adenine (A), guanine (G), cytosine (C), and thymine (T). In double stranded DNA,
adenine pairs with thymine (A-T) and guanine pairs with cytosine (G-C).
RNA Structure

RNA is essential for the synthesis of proteins. Information contained within the genetic code
is typically passed from DNA to RNA to the resulting proteins. There are several different
types of RNA.

• Messenger RNA (mRNA) is the RNA transcript or RNA copy of the DNA message
produced during DNA transcription. Messenger RNA is translated to form proteins.
• Transfer RNA (tRNA) has a three-dimensional shape and is necessary for the
translation of mRNA in protein synthesis.
• Ribosomal RNA (rRNA) is a component of ribosomes and is also involved in protein
synthesis.
• MicroRNAs (miRNAs) are small RNAs that help to regulate gene expression.

RNA most commonly exists as a single stranded molecule composed of a phosphate-ribose

sugar backbone and the nitrogenous bases adenine, guanine, cytosine and uracil (U). When
DNA is transcribed into an RNA transcript during DNA transcription, guanine pairs with
cytosine (G-C) and adenine pairs with uracil (A-U)

Differences Between DNA and RNA Composition

This image shows a comparison of a single-stranded RNA molecule and a double-stranded
DNA molecule

The nucleic acids DNA and RNA differ in composition and structure. The differences are
listed as follows:

DNA

Nitrogenous Bases: Adenine, Guanine, Cytosine, and Thymine

Five-Carbon Sugar: Deoxyribose
Structure: Double-stranded
DNA is commonly found in its three-dimensional, double helix shape. This twisted structure
makes it possible for DNA to unwind for DNA replication and protein synthesis.

RNA

Nitrogenous Bases: Adenine, Guanine, Cytosine, and Uracil

Five-Carbon Sugar: Ribose
Structure: Single-stranded
While RNA does not take on a double helix shape like DNA, this molecule is able to form
complex three-dimensional shapes. This is possible because RNA bases form complementary
pairs with other bases on the same RNA strand. The base pairing causes RNA to fold forming
various shapes.
Purines and Pyrimidines
Pyrimidines
A pyrimidine is an organic ring consisting of six atoms: 4 carbon atoms and 2 nitrogen atoms.
The nitrogen atoms are placed in the 1 and 3 positions around the ring. Atoms or groups
attached to this ring distinguish pyrimidines, which include cytosine, thymine, uracil,
thiamine (vitamin B1), uric acid, and barbituates. Pyrimidines function in DNA and RNA,
cell signaling, energy storage (as phosphates), enzyme regulation, and to make protein and
starch.

Purines
A purine contains a pyrimidine ring fused with an imidazole ring (a five-member ring with
two non-adjacent nitrogen atoms). This two-ringed structure has nine atoms forming the ring:
5 carbon atoms and 4 nitrogen atoms. Different purines are distinguished by the atoms or
functional groups attached to the rings.

Purines are the most widely occurring heterocyclic molecules that contain nitrogen. They are
abundant in meat, fish, beans, peas, and grains. Examples of purines include caffeine,
xanthine, hypoxanthine, uric acid, theobromine, and the nitrogenous bases adenine and
guanine. Purines serve much the same function as pyrimidines in organisms. They are part of
DNA and RNA, cell signaling, energy storage, and enzyme regulation. The molecules are
used to make starch and proteins.

Bonding Between Purines and Pyrimidines

While purines and pyrimidines include molecules that are active on their own (as in drugs
and vitamins), they also form hydrogen bonds between each other to link the two strands of
the DNA double helix and to form complementary molecules between DNA and RNA. In
DNA, the purine adenine bonds to the pyrimidine thymine and the purine guanine bonds to
the pyrimidine cytosine. In RNA, adenine bonds to uracil and guanine still bonds with
cytosine. Approximately equal amounts of purines and pyrimidines are required to form
either DNA or RNA.

It's worth noting there are exceptions to the classic Watson-Crick base pairs. In both DNA
and RNA, other configurations occur, most often involving methylated pyrimidines. These
are called "wobble pairings."

Comparing and Contrasting Purines and Pyrimidines

The purines and pyrimidines both consist of heterocyclic rings. Together, the two sets of
compounds make up the nitrogenous bases. Yet, there are distinct differences between the
molecules. Obviously, because purines consist of two rings rather than one, they have a
higher molecular weight. The ring structure also affects the melting points and solubility of
the purified compounds.

The human body synthesizes (anabolism) and breaks down (catabolism) the molecules
differently. The end product of purine catabolism is uric acid, while the end products of
pyrimidine catabolism are ammonia and carbon dioxide. The body does not make the two
molecules in the same location, either. Purines are synthesized primarily in the liver, while a
variety of tissues make pyrimidines.

Here is a summary of the essential facts about purines and pyrimidines:

Purine
Structure Double ring (one is a pyrimidine) Single ring
Chemical C5H4N4 C4H4N2
Formula
Nitrogenous Adenine, guanine Cytosine, uracil, thymine
Bases
Uses DNA, RNA, vitamins, drugs (e.g., DNA, RNA, drugs (e.g., stimulants),
barbituates), energy storage, protein and energy storage, protein and starch
starch synthesis, cell signaling, enzyme synthesis, enzyme regulation, cell
regulation signaling
Melting 214 °C (417 °F) 20 to 22 °C (68 to 72 °F)
Point
Molar Mass 120.115 g·mol−1 80.088 g mol−1
Solubility 500 g/L Miscible
(Water)
Biosynthesis Liver Various tissues
Catabolism Uric acid Ammonia and carbon dioxide
Product