Chemistry Reference
In-Depth Information
adenine
nicotinamide
NH
2
CONH
2
N
O
P
O
CONH
2
N
P
N
CH
2
O
O
O
CH
2
N
N
nicotinamide
CH
2
N
O
O
OH
OH
O
O
≡
RO
OH
O
P
OH
HO
OH
OH
NH
2
HO
O
R = H, NAD
+
R =
P
, NADP
+
N
O
P
OH
N
nicotinamide
O
adenine
CH
2
N
N
O
adenine
nicotinamide
ribose
P
≡
ribose
P
P
ribose
HO
OR
adenine
P
P
ribose
P
O
O
flavin
flavin
adenine
H
3
C
N
H
3
C
N
NH
NH
NH
2
H
3
C
N
N
O
H
3
C
N
N
O
N
O
P
O
N
OH
OH
P
N
CH
2
O
O
O
O
N
≡
OH
OH
OH
OH
OH
OH
O
O
P
OH
HO
OH
FMN
NH
2
O
FAD
O
P
OH
N
N
O
flavin
CH
2
N
N
adenine
O
ribitol
P
adenine
flavin
≡
HO
OR
ribose
P
P
ribitol
adenine
ribose
P
Box 14.3
Cyclic AMP
The nucleotide
cyclic AMP
(3
,5
-cyclic adenosine monophosphate,
cAMP
) is a cyclic phosphate ester of
particular biochemical significance. It is formed from the triester ATP by the action of the enzyme
adenylate
cyclase
, via nucleophilic attack of the ribose 3
-hydroxyl onto the nearest P
=
O group, displacing diphosphate as
leaving group. It is subsequently inactivated by hydrolysis to 5
-AMP through the action of a phosphodiesterase
enzyme.
