NUCLEIC ACID STRUCTURE

Components of DNA and RNA

1. Bases of DNA and RNA (bicyclic)
– The nitrogenous bases of DNA and
RNA are Adenine (A) and guanine (G),
cytosine (C), thymine (T) and Uracil
(U).
– A, T, G and C are found in DNA.
– A, U, G, and C are found in RNA (i.e. T
(monocyclic)
base is replaced by U in RNA).
– Thymine differs from Uracil only in
having a methyl group at
– the 5-position, i.e. thymine is 5-
methyluracil.
 NUCLEIC ACID STRUCTURE
Components of DNA and RNA
1. Bases of DNA and RNA
 NUCLEIC ACID STRUCTURE
Components of DNA and RNA

2. Sugar of DNA and RNA

– The sugars of nucleic acids — called
pentose sugars— have five carbon
atoms, numbered 1′, 2′, 3′, and so
forth.

– In DNA, the sugar is called 2-

deoxyribose.

– In RNA, the sugar is called ribose.

– In deoxyribose the hydroxyl group at

the 2-position is replaced by a
hydrogen, and so the prefix is ‘deoxy’.
 NUCLEIC ACID STRUCTURE
Components of DNA and RNA

3. Phosphate group
– a phosphorus-containing region known as a phosphate group.
 NUCLEIC ACID STRUCTURE
Components of a nucleoside
• Nucleoside
– In nucleic acids, the bases are covalently attached to the 1-position of
a pentose sugar ring, to form a nucleoside.

In case of In case of
ribose sugar deoxyribose sugar
 NUCLEIC ACID STRUCTURE
Components of a nucleoside

• Nucleoside
– The point of attachment to the base is the 1-position (N-1) of the
pyrimidines and the 9-position (N-9) of the purines.

1 9 9
1
 NUCLEIC ACID STRUCTURE
Components of a nucleoside

• Nucleoside
– The bond between the bases and the sugars is the N-glycosylic (or
N-glycosidic) bond.
 NUCLEIC ACID STRUCTURE
Components of a nucleoside

• Nucleoside
– How does glycosylic or glycosidic bond form?

Condensation
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide
– A nucleotide is a nucleoside attached to one or more phosphate groups
through phosphoester bond.

A nucleotide
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide
– Four types of bases
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide
– One or more phosphate groups bound covalently to the 3-, 5- or 2-
position (in ribonucleotides only).
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide
– If the sugar is ribose, then the compounds are termed ribonucleotides.

– If the sugar is deoxyribose, then the compounds are termed

deoxynucleotides.
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide

– In the case of the 5-position, up to three phosphates may be attached,

to form, for example, adenosine 5-triphosphate (ATP), or
deoxyguanosine 5-triphosphate (dGTP).

– In the same way, we have dCTP, UTP and dTTP (equivalent to TTP).

– 5-Mono and -diphosphates are abbreviated as, for example, AMP and
dGDP.
 NUCLEIC ACID STRUCTURE
Components of a nucleotide

• Nucleotide

– Nucleoside 5-triphosphates (NTPs), or deoxynucleoside 5-

triphosphates (dNTPs) are the building blocks of the polymeric nucleic
acids.

– In the course of DNA or RNA synthesis, two phosphates are split off as
pyrophosphate to leave one phosphate per nucleotide incorporated
into the nucleic acid chain.

– The repeat unit of a DNA or RNA chain is hence a polynucleotide.

NUCLEIC ACID STRUCTURE
Components of a nucleoside and nucleotide

Please! Please!
Make the long
story short.
 NUCLEIC ACID STRUCTURE
Nucleoside and Nucleotide nomenclature

• If the sugar is ribose (as in RNA), the nucleosides

(technically ribonucleosides) are adenosine, guanosine,
cytidine and uridine.
• If the sugar is deoxyribose (as in DNA), the nucleosides
(technically 2-deoxyribonucleosides) are deoxyadenosine,
deoxyguanosine, deoxycytidine and deoxythymidine.
• Thymidine and deoxythymidine may be used
interchangeably.
 NUCLEIC ACID STRUCTURE
Nucleoside and Nucleotide nomenclature
Base Nucleoside Nueleotide Nucleic acid
Purines
Adenine Adenosine Adenylate/Adenosine 5′- RNA
Deoxy(ribo)adenosin monophosphate DNA
e Deoxy(ribo)adenylate/Deox
yadenosine 5′-
monophosphate
Guanine Guanosine Guanylate/Guanosine 5′- RNA
Deoxyguanosine monophosphate DNA
Deoxy(ribo)guanylate/Deox
yguanosine 5′-
monophosphate
 NUCLEIC ACID STRUCTURE
Nucleoside and Nucleotide nomenclature
Base Nucleoside Nueleotide Nucleic acid
Pyrimidines
Cytosine Cytidine Cytidylate/ RNA
Deoxy(ribo)cytidine Cytidine 5′-monophosphate DNA
Deoxy(ribo)cytidylate/
Deoxycytidine 5′-
monophosphate
Thymine Thymidine or Thymidylate/ DNA
deoxy(ribo)thymidine Deoxythymidylate/
Deoxythymidine 5′-
monophosphate
Uracil Uridine Uridylate/ RNA