Nucleic Acids

Learning Objectives
Function of nucleic acids and nucleotides Bases, nucleosides, and nucleotides Complementary base pairing Double helix The genetic code

Functions
Nucleic acids DNA and RNA are polymers responsible for storage, propagation, and expression of genetic information Nucleotides are monomeric components of the nucleic acids Free nucleotides and their derivatives are involved in metabolic processes not related to the management of genetic information

Functions
Nucleotide derivatives function as energy carriers (e.g., ATP, adenosine triphosphate) and coenzymes (e.g., NAD+, nicotinamide adenine dinucleotide)

Nitrogenous Bases
Nucleotides, the monomeric components of DNA and RNA, are composed of a nitrogenous base linked to a sugar to which a phosphate group is attached Bases are structural derivatives of either purine or pyrimidine
N N N N N H N

purine

pyrimidine

Bases are planar, aromatic, heterocyclic molecules

Base, Nucleoside, and Nucleotide

NH2 N N N N N
5

NH2 N N

NH2 N

N H
4

N
5 2-O P-O-CH 3 2

N
O H
2 1

CH3 H
3

O H
2 1

H
3

OH

OH

OH

OH

Base Adenine

Nucleoside Adenosine

Nucleotide Adenosine monophosphate

The Five Common Bases

NH2 N N N H N N N O N H H2N N H

Adenine (A)
NH2 H N O N H O N N H O

Guanine (G)
O CH3 H N O N H

Cytosine (C)

Thymine (T)
(DNA)

Uracil (U)
(RNA)

Watson-Crick Pairs of Bases

H
N

H
N

CH3
N

N
N

N N
O

N N Ribose

Ribose

Ribose

N
N H H O

Ribose

Adenine-Thymine A-T

Guanine-Cytosine G-C

Ribonucleotides and Deoxyribonucleotides

5 2-O P-O-CH 3 2 4

Base

O H
2 1

5 2-O P-O-CH 3 2 4

Base

O H
2 1

H
3

H
3

OH

OH

OH

Ribonucleotide Sugar = ribose Component of ribonucleotide acids (RNAs)

Deoxyribonucleotide Sugar = 2 deoxyribose Component of deoxyribonucleotide acids (DNAs)

Chemical Structure of Nucleic Acids

Nucleic acids are polynucleotides Neighboring nucleotides are linked via phosphodiester bond. Terminal nucleotides have 5 and 3 atoms not linked to another nucleotide. They are called 5 end and 3 end, respectively.

Fig. 3-3

Chemical Structure of Nucleic Acids

By convention, a polynucleotide sequence is written with the 5 end at the left and the 3 end at the right DNA has equal numbers of adenine and thymine residues and equal numbers of guanine and cytosine residues

Fig. 3-3

The Double Helix

Polynucleotide chains wind around a common axis to form a double helix

Fig. 3-6

Two strands of DNA are antiparallel (run in opposite directions) The bases occupy the core of the helix and sugar-phosphate chains are on the periphery DNA surface has major and minor grooves

The Double Helix

Fig. 3-8

Bases at opposite strands are hydrogenbonded to form complementary pairs

The Genetic Code

Genetic code is the correspondence between nucleic acid sequences and polypeptide sequences A triplet of bases forms a codon that specifies a single amino acid.

Table 26-1

The Genetic Code

Genetic code is degenerate because the number of possible combinations of three bases (43=64) is much larger than the number of standard amino acids (20). The arrangement of the genetic code table is nonrandom.

The Genetic Code

Stop codons UAG, UAA, and UGA specify the end point of the polypeptide chain. Chain initiator codons AUG and GUG specify the starting point of the polypeptide chain.