Organic Chemistry

(Dana P.) #1

036 CHAPTER 27 Nucleosides, Nucleotides, and Nucleic Acids


Because phosphoric acid can form an anhydride, nucleotides can exist as monophos-
phates, diphosphates, and triphosphates. They are named by adding monophosphateor
diphosphateor triphosphateto the name of the nucleoside.

PROBLEM 2

Draw the structure for each of the following:

a. dCDP c. dUMP e. guanosine
b. dTTP d. UDP f. adenosine

27.2 ATP: The Carrier of Chemical Energy


All cells require energy to ensure their survival and reproduction. They get the
energy they need by converting nutrients into a chemically useful form of energy.
The most important form of chemical energy is adenosine -triphosphate (ATP).
The importance of ATP to biological reactions is shown by its turnover rate in hu-
mans—each day, a person uses an amount of ATP equivalent to his or her body
weight. ATP is known as the universal carrier of chemical energy because, as it is
commonly stated,“the energy of hydrolysis of ATP converts endergonic reactions
into exergonic reactions.”
In other words, the ability of ATP to enable otherwise unfavorable reactions to
occur is attributed to the large amount of energy released when ATP is hydrolyzed,
which can be used to drive an endergonic reaction. For example, the reaction of

5 ¿

3 ¿-monophosphate

5 ¿-triphosphate

phosphoric acid pyrophosphoric acid triphosphoric acid

O

OH

P
+


5 HO OH P 2 O 5 O

O

OH

P
OH

O

OH

P
HO O

O

OH

P
O

O

OH

P
OH

O

OH

P
HO

N

N

N

N

−O O

O

P

O−

NH 2

O

HO OH
adenosine
5 ′-monophosphate
AMP

N

N

N

N

O O

O

P

O−

−O

O

P

O−

NH 2

O

HO OH
adenosine
5 ′-diphosphate
ADP

N

N

N

N

O O

O

P

O−

−O

O

P

O−

O

O

P

O−

NH 2

O

HO OH
adenosine
5 ′-triphosphate
ATP

N

N

N

N

−O O

O

P

O−

NH 2

O

HO
2 ′-deoxyadenosine
5 ′-monophosphate
dAMP

N

N

N

N

O O

O

P

O−

−O

O

P

O−

NH 2

O

HO
2 ′-deoxyadenosine
5 ′-diphosphate
dADP

N

N

N

N

O O

O

P

O−

−O

O

P

O−

O

O

P

O−

NH 2

O

HO
2 ′-deoxyadenosine
5 ′-triphosphate
dATP
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