Professional Documents
Culture Documents
1495017622module 2 Etext
1495017622module 2 Etext
1495017622module 2 Etext
2. Concept Map
Nucleic acids
Nitrogenous Cyclic
Discovery Sugars Phosphate DNA and RNA
bases nucleotides
Purines and
Function
pyrimidines
Properties of purines
Types
and pyrimidines
Chargaff's rule
Nucleic acids constitute the most important biomolecules of the cell and are critical entities for all known
forms of life.
Discovery: Nucleic acids were discovered by Friedrich Miescher in 1869. He reported that he had found a
substance within the nuclei of human white blood cells, which was weakly acidic in nature and whose function
was unknown. He had named this material as "nuclein". A few years later, Miescher was successfully able to
separate nuclein into protein and nucleic acid components.
Nuclein was later named as nucleic acid in 1889 by Richard Altmann. They were so named because of their
initial discovery from within the nucleus (~nucle), and due to the presence of phosphate groups in their
molecules (phosphoric acid ~ ic acid).
Function: Nucleic acids are present in all living beings as well as in bacteria, archaea, mitochondria,
chloroplasts, viruses and viroids. Nucleic acids are involved in the storage and transfer of genetic information in
living organisms.
Types: There are two types of nucleic acids in cells, Deoxyribonucleic acid (DNA) and Ribonucleic acid (RNA).
Both DNA and RNA are the molecular repositories of genetic data.
The basic components of a nucleic acid include three different entities, namely a nitrogenous base, a sugar
moiety and a phosphate group. These combine to give one unit of a nucleotide (discussed later), which are
stacked in a nucleic acid molecule (Fig. 1).
The basic components of a nucleic acid are discussed in detail in sections below:
Inside the cells, five major nucleobases or nitrogenous bases are found. The derivatives of purine are called
adenine (A) and guanine (G) bases, while the derivatives of pyrimidine are called thymine (T), cytosine (C ) and
uracil (U) bases. The DNA contains A, G, C and T, whereas RNA contains A, G, C and U bases. The chemical
structures of the principal bases in nucleic acids are shown in Fig. 3.
Tautomerism: Both purines and pyrimidines exhibit keto-enol tautomerism. The keto tautomer is known
as a lactam ring, whereas the enol tautomer is known as a lactim ring. At neutral pH, the keto-tautomer
remains the more predominanting form. Upon interaction with other molecules, ring nitrogens in the
lactam serve as donors of hydrogen bond (H-bond), and the keto oxygens behave as H-bond acceptors.
Purines and pyrimidines, being complementary bases, can participate in base pairing, based on the specific
shapes and hydrogen bond properties.
Guanidine, being a complement of cytosine, pairs with cytosine through three hydrogen bonds. Adenine (A) is
the complement of thymine (T) in DNA and uracil (U) in RNA. Adenine base pairs with thymine and uracil
through two hydrogen bonds.
Chargaff’s Rule
Erwin Chargaff (1905-2002), an Austrian-American biochemist gave the Chargaff's rule, according to which
DNA always contains equal amounts of certain base pairs.
He observed that the amount of adenine (A) always equalled with the amount of thymine (T), and the amount
of guanine (G) always equalled the amount of cytosine (C), regardless of the DNA source.
The ratio of (A+T) to (C+G) varied from 2.70 to 0.35 in various organisms.
3.1.2 Sugars
Two types of pentose sugars are found in nucleic acids, namely ribose and 2-deoxy ribose. The carbons in the
ribose sugar are numbered according to convention. Ribose differs from deoxyribose in the presence of a
hydroxyl group at the 2’C. The structures of both ribose and deoxyribose are shown in Fig. 8. The D-ribose and
D-deoxyribose are found in RNA and DNA respectively, in their furanose (closed five-membered ring) forms.
3.1.3 Phosphates
Phosphate is another important component of the nucleic acid molecule. It gets attached to C-5’ OH group of
the sugar and gets incorporated into nucleic acid (both DNA and RNA).
3.2 Nucleosides
Fig.9. Nucleoside
3.3 Nucleotides
Nucleotides comprises of a nitrogenous base linked to a 5-carbon sugar and one or more phosphate group. The
phosphate is attached to 5’ CH2 OH group of sugar part of nucleoside. They function as the building blocks of
nucleic acids.
Nucleotides = nitrogenous base + sugar + phosphate
Nucleotides = Nucleosides + phosphate
10
Formation of nucleotide: The base of a nucleotide (position N-1 of pyrimidines or N-9 of purines) is forms a
covalent N—glycosyl bond with the 1’ carbon of the pentose, by removal of a water molecule. The phosphate
is esterified to the 5’ carbon (Fig. 12).
11
Nucleotide di- and tri-phosphates: The term "nucleotide" generally refers to a nucleoside monophosphate,
But in case additional phosphoric acid groups are present, they can link to the existing phosphate (in
nucleotide monophosphates) to produce nucleotide diphosphates and nucleotide tri-phosphates (Fig. 14).
Nucleoside monophosphates can sometimes form two ester bonds with the phosphoric acid, at the 5' and 3'
hydroxyl groups of the ribose sugar. This therefore results in the formation of cyclic nucleotides. These are
designated as cNMP where “c” stands for cyclic and “N” stands for the respective nucleoside.
12
Figure 15 above shows a cyclic guanosine monophosphate (cGMP). Cyclic AMP (cAMP) and cyclic GMP (cGMP)
are the two of the well-studied cyclic nucleotides. These are found in all cells and play important role in the
regulation of cell metabolism.
3.5 Polynucleotides
A polynucleotide formation is initiated when many nucleotides continue to join together by phosphodiester
linkages. The formation of polynucleotide is catalyzed by polymerase enzymes (DNA polymerase in case of DNA
or RNA polymerase in case of RNA). The -OH group on the 3’-carbon of sugar in one nucleotide reacts with the
13
DNA and RNA are examples of polynucleotides (Fig. 17), where the nucleotides are arranged in linear way and
proceeds in the 5' ----> 3' direction. A common representation of polynucleotide is given below:
5'pApTpGpC OH3'
While RNA is single stranded, DNA is double stranded and contains two such polynucleotide chains spiralling
round each other to form a double helical structure. The two chains in the double helix are held together by
hydrogen bonds by complementary bases on different chains.
14
Summary
Nucleic acids are important cellular biomolecules involved in the storage and transfer of genetic
information in all living organisms.
There are two types of nucleic acids in cells, Deoxyribonucleic acid (DNA) and Ribonucleic acid (RNA).
Nucleic acids include three different entities, namely a nitrogenous base, a sugar moiety and a
phosphate group.
o Bases are nitrogen-containing molecules, which are derivatives of purine and pyrimidine. Five
major bases found in cells are adenine (A) and guanine (G) (purine bases), thymine (T),
cytosine (C ) and uracil (U) bases (pyrimidine bases).
o The purines and the pyrimidines are complementary bases. Base pairing occurs between G and
C, A and T.
o Chargaff’s rule: Amount of adenine (A) equals the amount of thymine (T), and amount of
guanine (G) equals the amount of cytosine (C).
o Ribose and 2-deoxy ribose are two types of pentose sugars found in nucleic acids.
Nucleotides = nitrogenous base + sugar + phosphate.
Nucleotides = Nucleosides + phosphate; Nucleosides = nitrogenous base + sugar.
15
16