116

PANEL 26: A Survey of the Nucleotides

NUCLEOTIDES

PHOSPHATES

A nucleotide consists of a nitrogen-containing

base, a five-carbon sugar, and one or more
phosphate groups.

The phosphates are normally joined to

the C5 hydroxyl of the ribose or
deoxyribose sugar (designated 5'). Mono-,
di-, and triphosphates are common.

BASIC SUGAR
LINKAGE

N-glycosidic
bond

BASE
O

NH2

CH2

O
O

as in
ADP

CH2

Nucleotides
are the
subunits of
the nucleic acids.

OH

OH

SUGAR

O
P

CH2

as in
ATP

The base is linked to

the same carbon (C1)
used in sugarsugar
bonds.

The phosphate makes a nucleotide

negatively charged.

NH2

HC

cytosine
C

N
H

N
H

The bases are nitrogen-containing ring

compounds, either pyrimidines or purines.

uracil

4
5

N
7

3N

C
NH

C
HC
thymine

1
N

1N

PYRIMIDINE

PURINE

HOCH2

a five-carbon sugar

O
1
3

4
2

H
OH

two kinds are used

HOCH2

Each numbered carbon on the sugar of a nucleotide is

followed by a prime mark; therefore, one speaks of the
5-prime carbon, etc.

NH
C

NH2

b-D-ribose
used in ribonucleic acid

OH
OH

b-D-2-deoxyribose
used in deoxyribonucleic acid

H
OH

N
H

OH

C 5

C
C

HC
guanine

SUGARS

PENTOSE

3
N

N
H

CH
N
O

9
N

N
H

H3C

HC

adenine

NH

HC

C
NH2

BASES

HC

SUGAR

O
3

HC

BASE
5

as in
AMP

CH2

PHOSPHATE

CHAPTER 2 PANELS

117

NOMENCLATURE

A nucleoside or nucleotide is named according to its nitrogenous base.

base
Single letter abbreviations are used variously as
shorthand for (1) the base alone, (2) the
NUCLEOSIDE
ABBR.
nucleoside, or (3) the whole nucleotide
sugar
the context will usually make clear which of
adenosine
A
the three entities is meant. When the context
is not sufficient, we will add the terms base, BASE + SUGAR = NUCLEOSIDE
guanosine
G
nucleoside, nucleotide, oras in the
examples belowuse the full 3-letter nucleotide
cytidine
C
base
code.

BASE
adenine
guanine
cytosine
uracil

uridine

thymine

thymidine

NUCLEIC ACIDS

AMP
dAMP
UDP
ATP

NUCLEOTIDES HAVE MANY OTHER FUNCTIONS

Nucleotides are joined together by a

phosphodiester linkage between 5 and
3 carbon atoms to form nucleic acids.
The linear sequence of nucleotides in a
nucleic acid chain is commonly
abbreviated by a one-letter code,
AGCTTACA, with the 5
end of the chain at the left.

O
O

They carry chemical energy in their easily hydrolyzed phosphoanhydride bonds.

CH2

NH2

phosphoanhydride bonds

N
O
O

O
O

CH2

OH

example: ATP (or ATP )

OH

sugar

O
P

base

= adenosine monophosphate
P
= deoxyadenosine monophosphate
sugar
= uridine diphosphate
= adenosine triphosphate
BASE + SUGAR + PHOSPHATE = NUCLEOTIDE

OH
2

NH2

They combine with other groups to form coenzymes.

base

O
sugar

HS

OH

N
H

N
H

H CH3 H

O
O

CH2

HO CH3 H

example: coenzyme A (CoA)

O

5 end of chain

5
CH2

base

O
3

sugar

3 O
P

They are used as specific signaling molecules in the cell.

example: cyclic AMP (cAMP)

example: DNA

O
5 CH2

P
O

NH2
phosphodiester
O
linkage

CH2

base

CH2

N
O

sugar

O
3 OH
3 end of chain

P
O

OH

OH