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Bch 341-Lecture 2

Nucleic acids, including RNA and DNA, are essential macromolecules that encode genetic information and consist of nucleotides linked by phosphodiester bonds. The structure of nucleotides includes a sugar (ribose in RNA and deoxyribose in DNA), a nitrogenous base (pyrimidines and purines), and one or more phosphate groups. Nucleic acids play crucial roles in heredity, protein synthesis, and forensic identification through DNA fingerprinting.

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Bch 341-Lecture 2

Nucleic acids, including RNA and DNA, are essential macromolecules that encode genetic information and consist of nucleotides linked by phosphodiester bonds. The structure of nucleotides includes a sugar (ribose in RNA and deoxyribose in DNA), a nitrogenous base (pyrimidines and purines), and one or more phosphate groups. Nucleic acids play crucial roles in heredity, protein synthesis, and forensic identification through DNA fingerprinting.

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BCH 341

CHEMISTRY OF NUCLEIC ACID BASES, NUCLEOTIDES & POLYNUCLEOTIDES

Nucleic acids, RNA and DNA, which are the biochemical macromolecules encoding genetic
information, have been known as chemicals since the 19th century. Friedrich Miescher first
isolated them from nuclei of white blood cells in 1869. He called it “nuclein”. However, their
vast biological significance was not appreciated until the 1940s.
Nucleic acids are linear polymers like proteins. Proteins are made by connecting amino acids
via peptide bonds. Nucleic acids are made by connecting nucleotides via phosphodiester bonds.
The repeating unit is the nucleotide. The nucleotide, in turn, is built from three components: a
sugar, a base, and a phosphate group. There are two types of the nucleic acid sugars and four
different bases.

The backbone of a nucleic acid is built from the sugars, linked together by the phosphates. This
is called “sugar-phosphate backbone”. The bases (which carry the genetic sequence
information) are linked to the sugars.

1) SUGAR
D-Ribose is the sugar in RNA. It’s a pentose aldose sugar. DNA is deoxyribonucleic acid and
its sugar is D-2-deoxyribose. It’s an unusual sugar: one of the -OH groups – the one at C2 – is
missing. Instead, that carbon is -CH2. That’s why it is called deoxyribose: an oxygen atom is
missing.
Deoxyribose is a reduced sugar: one C is reduced from -CH(OH) to -CH2 (methylene).
Deoxyribose, the DNA sugar, is so peculiar that its structure wasn’t figured out until about
1930, long after most other sugar structures were known. Both ribose and deoxyribose occur
in their β-furanose form.
2) BASES
The nitrogenous bases found in nucleic acids are derivatives of two parent compounds,
pyrimidines and purines.

Both DNA and RNA contain two major pyrimidine bases. One of them, cytosine (C) is found
in both DNA and RNA, but the second pyrimidine is different in DNA from what is found in
RNA: thymine (T) in DNA and uracil (U) in RNA. Thymine is just like uracil, except that it
has a methyl group at position 5. Therefore, thymine is also called “5-methyluracil”.

There are two purine bases in RNA and DNA. They are adenine and guanine. Adenine is 6-
aminopurine. Guanine is 6-oxo-2-aminopurine. Purines are bigger than pyrimidines. The
purine ring is a fused (joined together) bicyclic (two rings) heterocycle. There are four N atoms
and five C atoms in the purine ring system. Note that there are no N-N bonds: the N atoms are
always separated by at least one C atom.

3) NUCLEOSIDE AND NUCLEOTIDE


Nucleoside is a combination of a base and a sugar, lacking the phosphate group found in
nucleotides.
Base + sugar = Nucleoside.
Nucleotide is simply a nucleoside with one or more phosphate groups attached.
Base + Sugar + Phosphate → Nucleotide
Nucleotides are phosphorylated nucleosides.
The figure above shows a nucleotide in which phosphate is added to the 5′ -OH group of the
sugar. It is a deoxyribose 5′-phosphate.
RNA is very easily hydrolyzed; DNA is much more stable. RNA is hydrolyzed rapidly under
alkaline conditions, but DNA is not.

4) POLYNUCLEOTIDES

A chain of nucleotides attached together via a phosphodiester linkage at the 3′ and 5′ positions
of neighbouring ribose units are called polynucleotides. The sugar of a nucleotide is linked to
another via a phosphodiester bond. As seen in the figure above, a phosphate group bridges
between the 5′-OH of one nucleotide unit and the 3′-OH of another
Note: The phosphodiester bond is between the 5′ and the 3′ -OH groups. The 2′-OH of RNA is
not involved. So the linkage pattern is the same for DNA (which does not even have a 2′ -OH)
as it is for RNA.

THE FUNCTIONS OF NUCLEIC ACIDS

i) Nucleic acids are responsible for the transmission of inherent characters from parent to
offspring.

ii) They are responsible for the synthesis of protein in our body

iii) DNA fingerprinting is a method used by forensic experts to determine paternity. It is also
used for the identification of criminals. It has also played a major role in studies regarding
biological evolution and genetics.

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