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are similar to the concentration of reagents encountered in PET radiochemistry (nM to
C]glutamic acid (n = 2)
1,4-diamino-[4-11C]butyric acid
(a)
(b)
μM). Enzymatic reactions oer several advantages over traditional synthetic transformations, including their exceptional substrate selectivity, ability to facilitate reactions
under physiological conditions, and ability to provide enantiomerically pure products.
These same advantages do simultaneously limit the widespread application of enzymes
in PET radiochemistry. The use of enzymes in radiochemical syntheses is hampered by
the limited substrate tolerance, sensitivity to radiolabelling conditions (solvent, heating,
pH, and ionic strength), and particularly, in this case, sensitivity to radiolysis. The use of
immobilized enzymes has somewhat facilitated their use as it simplies separation of the
enzyme from the radiolabelled product, but concerns may arise from any residual potentially immunogenic protein. Despite these concerns, many enzymes have been explored
for the synthesis of
primary and secondary precursors (such as [
11
C-radiolabelled PET agents. Enzymes have been used to incorporate
11
C]CO2/[11C]HCO3 and [11C]CN−) into biological
molecules, as well as for further chemical transformations of molecules that have been
radiolabelled with carbon-11 either chemically or enzymatically.
The preparation of enantiopure
11
C-radiolabelled amino acids has been the primary
focus of applications of enzymes for PET as their chemical preparation is challenging
(vide supra). In an eort to prepare
bilized phosphoenol pyruvate carboxylase for the xation of [
pyruvate to give [4-
11
C]oxaloacetic acid (Figure7.62a). Further reaction with immobilized
11
l-[4-
C]aspartic acid, Barrio etal. employed immo-
11
C]CO2 with phosphoenol
O
*
O
NH
OH
2
C]aspartic acid
O
*
O
n
NH
OH
2
C]aspartic acid (n = 1)
or
HO
P
HO
OH
O
O OH
n
NH
O
OH
O
O
2
11
[
C]CO
2
phosphoenol
pyruvate
carboxylase
11
[
C]HCN
O-acetyl-L-serine
sulfhydrylase (n = 1)
HO
*
O
O
11
[4-
C]oxaloacetic acid
11
N
C
n
O
NH
OH
O
2
or
γ-cyano-α-aminobutyric
acid synthase (n = 2)
reduction
transaminase
OH
Aspartate
hydroysis
HO
L-[4-
L-[4-
L-[4-
11
HO
11
11
O
H2N
*
Figure 7.62
NH
OH
2
215
aspartate transaminase provided l-[4 -11C]aspartic acid in 10% RCY[470]. [11C]HCN has also
O
OH
(a)
(b)
[
C]tryptophan
been used as a substrate for enzymatic incorporation to provide amino acids. Enzymatic
reaction of [
nine and γ-[
can be further hydrolysed to provide
Reduction of β-[
11
C]HCN with O -acetylserine or O-acetylhomoserine gives β-[11C]cyano-l-ala-
11
C]cyano-α-amino-l-butyric acid, respectively (Figure7.62b). These products
11
l-[4-
C]aspartic acid and l-[5-11C]glutamic acid[471].
11
C]cyano-l-alanine has been used to prepare 1,4-diamino-[4-11C]butyric
acid[472]. Other amino acids that have been radiolabelled by enzymatic means from
simple precursors include [3-
11
from [
C]methanol[473]; and l-[methyl-11C]methionine, prepared from [11C]methanethiol
11
C]serine, prepared in a three-step enzymatic sequence
catalysed by immobilized γ-cyano-α-aminobutyric acid synthase[474].
O
*
11
[
C]acetic acid
NH
11
[
C]alanine
OH
O
OH
O
NMe
3
carnitine
carnitine
acetyl transferase
O
*
O-[11C]Acetylcarnitine
HO
OH
OH
O
HN
OH
*
acetyl CoA
synthetase
O
SCoA
*
11
[
C]acetyl CoA
glucosamine
N-acetyltransferase
O
11
C]Acetyl-D-glucosamine
N-[
serotonin
arylamine
N-acetyltransferase
HO
11
C]Acetylserotonin
N-[
N
H
O
N
*
H
O
phenol
β-tyrosinase
*
OH
*
2
transaminase or
D-amino acid oxidase
11
[
O
OH
*
O
C]pyruvic acid
HO
11
[
C]tyrosine
indole
tryptophanase
N
H
11
NH
NH
*
2
O
OH
*
2
Figure 7.63
216 Handbook of Radiopharmaceuticals
H
OH
[
C]acetoacetate
O
(c)
(d)
3
11
S
C
L-[
11
[
NH
C]leucine
cell free protein synthesis
O
OH
NH
2
11
C]methionine
ATP
SAM synthetase
O
OH
*
2
D-amino acid oxidase
11
H
C
3
COO
H3N
S-adenosyl-[
S
NH
11
[
C]interleukin 8
S
11
CH
3
HO
O
*
NH
2
L-[11C]leucine
N
H
2
N
N
O
OH
11
C]methionine
OH
NH
2
N
norepinephrine
N
methyl transferase
O
H
N
11
H
C
3
HO
HO
11
[
C]epinephrine
O
OH
*
(e)
OOHO
OHOHO
NADH
*
11
hydroxybutyrate dehydrogenase
D-β-hydroxy-[11C]butyrate
*
Figure 7.63
The second approach is to use a chemically prepared 11C-labelled substrate for the
enzyme (e.g. [
generate a more complex
the incorporation of
11
[
C]acetate by acetyl CoA-synthetase (Figure7.63a)[475]. Further enzymatic reactions cat-
alysed by acetyl transferases have been used and provide O-[
11
N-[
C]acetyl-d-glucosamine[478], and N-[11C]acetylserotonin[479]. Similarly, chemically
produced [
by either a transaminase or a
Pyruvate has been used as a substrate for the enzymatic synthesis of [
11
[
C]tryptophan[481–483]. In both cases, using either [11C]acetate or [11C]alanine labelled
11
C]acetate, l-[11C]alanine, or l-[11C]methionine) in an enzymatic reaction to
11
C-labelled biomolecules. This strategy has been applied to
11
C-acetyl groups via [11C]acetyl co-enzyme A (CoA), prepared from
11
C]alanine can be used for the enzymatic synthesis of [11C]pyruvate catalysed
d-amino acid oxidase, as shown in Figure7.63b[480]. [
11
C]acetylcarnitine[476, 477],
11
11
C]tyrosine and
C]
at either the carboxyl- or methyl-position provides PET radiotracers labelled at dierent sites, which have been used as a means to investigate in vivo metabolism of these
tracers[476].
l-[methyl-
11
C]Methionine prepared chemically from [11C]CH3I has also been
used for the direct incorporation of radiolabelled amino acids into peptides, such as the
single-chain variable fragment of an antibody and interleukin-8 (Figure7.63c)[484–486].
l-[methyl-
11
C]Methionine has also been combined with S-adenosylmethionine synthetase
217
and methyl transferases to selectively transfer a 11C-methyl group to an appropriate
nor-methyl precursor such as for the preparation of (–)-[
have also been used for the chiral resolution of chemically produced racemic
compounds[480]. Barrio etal. described the application of immobilized
oxidase and catalase as an ecient means to access enantioenriched
11
C]adrenaline[487]. Enzymes
11
C-labelled
d-amino acid
11
l-[
C]leucine
(Figure7.63d)[369]. Alternatively, the ability of enzymes to stereoselectively generate
chiral products from achiral precursors can be exploited, as described by Tremblay etal.,
where enzymatic reduction of a ketone stereoselectively provided
d-β-hydroxy-[
11
C]buty-
rate, as shown in Figure7.63e[488].
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