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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].
REFERENCES
1. Lauritsen, C.C., Crane, H.R., and Harper, W.W. (1934). Articial production of radioac-
tive substances. Science 79 (2045): 234–235.
2. Crane, H.R. and Lauritsen, C.C. (1934). Radioactivity from carbon and boron oxide
bombarded with deutons and the conversion of positrons into radiation. Physiol. Rev.
45 (6): 430–432.
3. Barkas, W.H. (1939). Some new reactions in light nuclei with high energy protons.
Physiol. Rev. 56 (3): 287–287.
4. Conti, M. and Eriksson, L. (2016). Physics of pure and non-pure positron emitters for
PET: a review and a discussion. EJNMMI Phys. 3 (1): 8.
5. Long, F.A. (1939). A study of the interchange between chromioxalate ion and oxalate
ion, using radio-carbon. J. Am. Chem. Soc. 61 (3): 570–572.
6. Ruben, S., Hassid, W.Z., and Kamen, M.D. (1939). Radioactive carbon in the study of
photosynthesis. J. Am. Chem. Soc. 61 (3): 661–663.
7. Tobias, C.A., Lawrence, J.H., Roughton, F.J.W. etal. (1945). The elimination of carbon
monoxide from the human body with reference to the possible conversion of CO to
CO
. Am. J. Physiol. Content 145 (2): 253–263.
8. Dahl, K., Halldin, C., and Schou, M. (2017). New methodologies for the preparation of
9. Welch, M.J. and Redvanly, C.S. (2002). Handbook of Radiopharmaceuticals (eds. M.J.
10. Pike, V.W., McCarron, J.A., Lammertsma, A.A. etal. (1996). Exquisite delineation of
11. Torstenson, R., Tedro, J., Hartvig, P. etal. (1999). A comparison of
12. Antoni, G. (2015). Development of carbon-11 labelled PET tracers - radiochemical and
13. Cohen, M.B., Spolter, L., Chia, C.C. etal. (1982). The varying tissue distribution of L-glu-
2
carbon-11 labeled radiopharmaceuticals. Clin. Transl. Imaging 5 (3): 275–289.
Welch and C.S. Redvanly). Chichester, UK: Wiley.
5-HT1A receptors in human brain with PET and [Carbonyl-
11
C]WAY-100635. Eur. J.
Pharmacol. 301 (1–3): R5–R7.
11
C-labeled
L-DOPA and L-uorodopa as positron emission tomography tracers for the presynaptic dopaminergic system. J. Cereb. Blood Flow Metab. 19 (10): 1142–1149.
technological challenges in a historic perspective. J. Labelled Compd. Radiopharm. 58
(3): 65–72.
tamic acid labelled at three dierent sites. Int. J. Appl. Radiat. Isot. 33 (8): 613–617.
218 Handbook of Radiopharmaceuticals
14. Pekošak, A., Filp, U., Poot, A.J., and Windhorst, A.D. (2018). From carbon-11-labeled
amino acids to peptides in positron emission tomography: the synthesis and clinical
application. Mol. Imaging Biol. 20 (4): 510–532.
15. McQuade, P., Rowland, D., Lewis, J., and Welch, M. (2005). Positron-emitting isotopes
produced on biomedical cyclotrons. Curr. Med. Chem. 12 (7): 807–818.
16. Crouzel, C., Långström, B., Pike, V.W., and Coenen, H.H. (1987). Recommendations
for a practical production of [
11
C]methyl iodide. Int. J. Radiat. Appl. Instrum. A Appl.
Radiat. Isot. 38 (8): 601–603.
17. Wilson, A.A., Garcia, A., Jin, L., and Houle, S. (2000). Radiotracer synthesis from [
11
C]-iodo-
methane: a remarkably simple captive solvent method. Nucl. Med. Biol. 27 (6): 529–532.
18. Kim, D., Alexo, D.L., Schueller, M. etal. (2014). The design and performance of a portable handheld
11
CO2 delivery system. Appl. Radiat. Isot. 94: 338–343.
19. Mock, B.H., Vavrek, M.T., and Mulholland, G.K. (1995). Solid-phase reversible trap for
11
[
C]carbon dioxide using carbon molecular sieves. Nucl. Med. Biol. 22 (5): 667–670.
20. Clark, J.C. and Buckingham, P.D. (1971). The preparation and storage of carbon-11
labelled gases for clinical use. Int. J. Appl. Radiat. Isot. 22 (11): 639–646.
21. Christman, D.R., Finn, R.D., Karlstrom, K.I., and Wolf, A.P. (1975). The production of
ultra high activity
11
C-labeled hydrogen cyanide, carbon dioxide, carbon monoxide
and methane via the reaction (XV). Int. J. Appl. Radiat. Isot. 26 (8): 435–442.
22. Eriksson, J., Hoek, J., and Windhorst, A.D. (2012). Transition metal mediated synthesis using [
11
C]CO at low pressure - a simplied method for 11C-carbonylation. J.
Labelled Compd. Radiopharm. 55 (6): 223–228.
23. Dahl, K., Itsenko, O., Rahman, O. etal. (2015). An evaluation of a high-pressure
11
CO
carbonylation apparatus. J. Labelled Compd. Radiopharm. 58 (5): 220–225.
24. Verbeek, J., Eriksson, J., Syvänen, S. etal. (2012). [
11
by [
C]CO carbonylation and rst evaluation as a P-Gp tracer in rats. EJNMMI Res.
11
C]phenytoin revisited: synthesis
2 (1): 36.
25. Clark, J.C. and Buckingham, P.D. (1975). Short-Lived Radioactive Gases for Clinical Use.
Oxford: Butterworth-Heinemann.
26. Kasyutich, V.L., McMahon, A., Barnhart, T., and Martin, P.A. (2008). On-line monitoring of cyclotron target-gas output by means of tunable lead salt diode laser
absorption spectroscopy. Appl. Phys. B 93 (2–3): 701–711.
27. Zeisler, S.K., Nader, M., Theobald, A., and Oberdorfer, F. (1997). Conversion of nocarrier-added [
synthesis of
28. Dahl, K., Ulin, J., Schou, M., and Halldin, C. (2017). Reduction of [
11
C]carbon dioxide to [11C]carbon monoxide on molybdenum for the
11
C-labelled aromatic ketones. Appl. Radiat. Isot. 48 (8): 1091–1095.
11
C]CO2 to [11C]CO
using solid supported zinc. J. Labelled Compd. Radiopharm. 60 (13): 624–628.
29. Roeda, D., Crouzel, C., and Dollé, F. (2004). A rapid, almost quantitative conversion of
11
[
C]carbon dioxide into [11C]carbon monoxide via [11C]formate and [11C]formyl chlo-
ride. Radiochim. Acta 92 (4–6): 329–332.
30. Nordeman, P., Friis, S.D., Andersen, T.L. etal. (2015). Rapid and ecient conversion
11
of
CO2 to 11CO through silacarboxylic acids: applications in Pd-mediated carbonyla-
tions. Chem. Eur. J. 21 (49): 17601–17604.
219
31. Taddei, C., Bongarzone, S., Haji Dheere, A.K., and Gee, A.D. (2015). [11C]CO2 to [11C]CO
conversion mediated by [
11
C]silanes: a novel route for [11C]carbonylation reactions.
Chem. Commun. 51 (59): 11795–11797.
32. Taddei, C., Bongarzone, S., and Gee, A.D. (2017). Instantaneous conversion of [
11
to [
C]CO via uoride-activated disilane species. Chem. Eur. J. 23 (32): 7682–7685.
33. Anders, D.A., Bongarzone, S., Fortt, R. etal. (2017). Electrochemical [
11
C]CO2 to [11C]
11
C]CO2
CO conversion for PET imaging. Chem. Commun. 53 (20): 2982–2985.
34. Långström, B., Antoni, G., Gullberg, P. etal. (1987). Synthesis of L- and D-[Methyl-
11
C]
methionine. J. Nucl. Med. 28 (6): 1037–1040.
35. Gómez-Vallejo, V. and Llop, J. (2009). Specic activity of [
11
C]CH3I synthesized by
the “Wet” method: main sources of non-radioactive carbon. Appl. Radiat. Isot. 67
(1) : 111–114.
36. Comar, D., Maziere, M., and Crouzel, C. (1973). Synthese et Metabolisme de
l’iodomethylaye de Chlorpromazine-
11
C. In: Radiopharmaceuticals and Labelled Com-
pounds, vol. 1, 461–469. Vienna: International Atomic Energy Agency.
37. Comar, D., Cartron, J.-C., Maziere, M., and Marazano, C. (1976). Labelling and metabolism of methionine-methyl-
38. Långström, B. and Lundqvist, H. (1976). The preparation of
its use in the synthesis of
11
C. Eur. J. Nucl. Med. 1 (1): 11–14.
11
C-methyl iodide and
11
C-methyl-L-methionine. Int. J. Appl. Radiat. Isot. 27
(7): 357–363.
39. Oberdorfer, F., Hanisch, M., Helus, F., and Maier-Borst, W. (1985). A new procedure
for the preparation of
11
C-labelled methyl iodide. Int. J. Appl. Radiat. Isot. 36
(6): 435–438.
40. Holschbach, M. and Schüller, M. (1993). A new and simple on-line method for the
preparation of n.c.a. [
11
C]methyl iodide. Appl. Radiat. Isot. 44 (4): 779–780.
41. Ferrieri, R.A. (2003). Synthetic precursors labeled with carbon-11 and uorine-18. In:
Handbook of Radiopharmaceuticals: Radiochemistry and Applications (eds. M.J. Welch
and C.S. Redvanly), 230–282.
42. Itsenko, O., Goméz-Vallejo, V., Llop, J., and Koziorowski, J. (2013). On
11
C chemistry
reviews - surveying and lling the gaps. Curr. Org. Chem. 17 (19): 2067–2096.
43. Gomez-Vallejo, V., Gaja, V., Koziorowski, J., and Llop, J. (2012). Specic activity of
11
C-labelled radiotracers: a big challenge for PET chemists. In: Positron Emission
Tomography - Current Clinical and Research Aspects, vol. 2 (ed. C.-H. Hsieh), 183–
210. InTech.
44. Ermert, J., Stüsgen, S., Lang, M. etal. (2008). High molar activity of [
11
[
C]methyl triate using the “Wet” [11C]CO2 reduction method. Appl. Radiat. Isot. 66
11
C]TCH346 via
(5): 619–624.
45. Matarrese, M., Soloviev, D., Todde, S. etal. (2003). Preparation of [
11
C] radioligands
with high specic radioactivity on a commercial PET tracer synthesizer. Nucl. Med.
Biol. 30 (1): 79–83.
46. Zhang, M.-R. and Suzuki, K. (2005). Sources of carbon which decrease the specic
activity of [
11
C]CH3I synthesized by the single pass I2 method. Appl. Radiat. Isot. 62
(3): 447–450.
220 Handbook of Radiopharmaceuticals
47. Iwata, R., Ido, T., Ujiie, A. etal. (1988). Comparative study of specic activity of [11C]
methyl iodide: a search for the source of carrier carbon. Int. J. Radiat. Appl. Instrum. A
Appl. Radiat. Isot. 39 (1): 1–7.
48. Link, J.M., Krohn, K.A., and Clark, J.C. (1997). Production of [
reaction of [
11
C]CH4 with I2. Nucl. Med. Biol. 24 (1): 93–97.
49. Larsen, P., Ulin, J., Dahlstrøm, K., and Jensen, M. (1997). Synthesis of [
ane by iodination of [
11
C]methane. Appl. Radiat. Isot. 48 (2): 153–157.
11
C]CH3I by single pass
11
C]iodometh-
50. Shao, X., Hoareau, R., Runkle, A.C. etal. (2011). Highlighting the versatility of the tracerlab synthesis modules. Part 2: fully automated production of [
11
C]-labeled radiopharma-
ceuticals using a tracerlab FXC-pro. J. Labelled Compd. Radiopharm. 54 (14): 819–838.
51. Noguchi, J. and Suzuki, K. (2003). Automated synthesis of the ultra high specic
activity of [
11
C]Ro15-4513 and its application in an extremely low concentration
region to an ARG study. Nucl. Med. Biol. 30 (3): 335–343.
52. Andersson, J., Truong, P., and Halldin, C. (2009). In-target produced [
11
C]methane:
increased specic radioactivity. Appl. Radiat. Isot. 67 (1): 106–110.
53. Wagner, R., Stöcklin, G., and Schaack, W. (1981). Production of carbon-11 labelled
methyl iodide by direct recoil synthesis. J. Labelled Compd. Radiopharm. 18 (11):
1557–1566.
54. Eriksson, J., Ulin, J., and Långström, B. (2006). [
11
C]Methyl iodide from [11C]methane
and iodine using a non-thermal plasma method. J. Labelled Compd. Radiopharm. 49
(13): 1177–1186 .
55. Någren, K., Müller, L., Halldin, C. etal. (1995). Improved synthesis of some commonly used PET radioligands by the use of [
11
C]methyl triate. Nucl. Med. Biol. 22
(2): 235–239.
56. Lundkvist, C., Sandell, J., Någren, K. etal. (1998). Improved syntheses of the PET
radioligands, [
11
C]FLB 457, [11C]MDL 100907 and [11C]β-CIT-FE, by the use of [11C]
methyl triate. J. Labelled Compd. Radiopharm. 41 (6): 545–556.
57. Jewett, D.M. (1992). A simple synthesis of [
11
C]methyl triate. Int. J. Radiat. Appl.
Instrum. 43 (11): 1383–1385.
58. Mock, B.H., Mulholland, G.K., and Vavrek, M.T. (1999). Convenient gas phase bromination of [
11
C]methane and production of [11C]methyl triate. Nucl. Med. Biol. 26
(4): 467–471.
59. Fei, X., Mock, B.H., DeGrado, T.R. etal. (2004). An improved synthesis of PET dopamine D
60. Madsen, J., Elfving, B., Andersen, K. etal. (2004). Gas phase production of [
methyl iodide-D
receptors radioligand [11C]raclopride. Synth. Commun. 34 (10): 1897–1907.
2
. Synthesis and biological evaluation Of S-[N-methyl-11C]citalopram
3
11
C]
and deuterated analogues. J. Labelled Compd. Radiopharm. 47 (6): 335–348.
61. Slegers, G., Sambre, J., Goethals, P. etal. (1986). Synthesis of [1the preparation of [
11
C]ethyl labelled radiopharmaceuticals. Int. J. Radiat. Appl.
11
C]iodoethane for
Instrum. A Appl. Radiat. Isot. 37 (4): 279–282.
62. Långström, B., Antoni, G., Gullberg, P. etal. (1986). The synthesis of 1-
11
C-labelled
ethyl, propyl, butyl and isobutyl iodides and examples of alkylation reactions. Int. J.
Radiat. Appl. Instrum. A Appl. Radiat. Isot. 37 (11): 1141–1145.
221
63. Antoni, G. and Langstrom, B. (1987). Asymmetric synthesis of L-2-amino[3-11C]butyric
acid, L-[3-
64. Rotteveel, L., Poot, A.J., Funke, U. etal. (2017). Radiosynthesis of 1-Iodo-2-[
ylpropane and 2-methyl-1-[
11
C]norvaline and L-[3-11C]valine. Acta Chem. Scand.: 511–517.
11
C]propanol and its application for alkylation reactions
11
C]meth-
and C—C bond formation. J. Labelled Compd. Radiopharm. 60 (12): 566–576.
65. Antoni, G. and Långström, B. (1987). Synthesis of racemic [3-
11
C]-labelled alanine, 2-ami-
nobutyric acid, norvaline, norleucine, leucine and phenylalanine and preparation of L-[3-
11
C]alanine and L-[3-11C]phenylalanine. J. Labelled Compd. Radiopharm. 24 (2): 125–143.
66. Dannals, R.F., Långström, B., Ravert, H.T. etal. (1988). Synthesis of radiotracers
for studying muscarinic cholinergic receptors in the living human brain using positron emission tomography: [
11
C]dexetimide and [11C]levetimide. Int. J. Radiat. Appl.
Instrum. A Appl. Radiat. Isot. 39 (4): 291–295.
67. Fasth, K.-J., Antoni, G., and Langström, B. (1988). Asymmetric synthesis of L-[3alanine and L-[3-
11
C]phenylalanine by a phase-transfer alkylation reaction. J. Chem.
11
C]
Soc. Perkin Trans. 1 0 (12): 3081–3084.
68. Fasth, K.J., Antoni, G., and Långström, B. (1990). Synthesis of some α-
11
C-labelled
substituted benzyl iodides. Int. J. Radiat. Appl. Instrum.A Appl. Radiat. Isot. 41
(6): 611–613.
69. Zhang, M.-R., Ogawa, M., Maeda, J. etal. (2006). [2-
11
[
C]methyl-labeled phenoxyphenyl acetamide derivatives as positron emission
11
C]isopropyl-, [1-11C]ethyl-, and
tomography ligands for the peripheral benzodiazepine receptor: radiosynthesis,
uptake, and in vivo binding in brain. J. Med. Chem. 49 (9): 2735–2742.
70. Halldin, C., Bjurling, P., Stålnacke, C.-G. etal. (1989).
11
C-labelling of dimethylphenethylamine in two dierent positions and biodistribution studies. Int. J. Radiat.
Appl. Instrum. A Appl. Radiat. Isot. 40 (7): 557–560.
71. Eriksson, J., Antoni, G., and Långström, B. (2004). Synthesis of [1-
11
from[
C]carbon monoxide and its application in alkylation reactions. J. Labelled
11
C]ethyl iodide
Compd. Radiopharm. 47 (11): 723–731.
72. Eriksson, J., Antoni, G., and Långström, B. (2006). Synthesis of [1-
11
[1-
C]butyl iodide from [11C]carbon monoxide and their use in alkylation reactions. J.
11
C]propyl and
Labelled Compd. Radiopharm. 49 (12): 1105–1116.
73. Cramer, R.D. and Kistiakowsky, G.B. (1941). Synthesis of radioactive lactic acid. J. Biol.
Chem. 137 (3): 549–555.
74. Labaree, D.C., Ropchan, J.R., Nabulsi, N., and Huang, Y. (2017). A modication to
improve the reliability of [
11
C]CN− production in the GE radiochemistry system. J.
Labelled Compd. Radiopharm. 60 (12): 592–595.
75. Christman, D.R., Finn, R.D., Karlstrom, K.I., and Wolf, A.P. (1973). Production of carrier-free H
11
CN for medical use and radiopharmaceutical syntheses. IX. J. Nucl. Med.
14 (11): 864–866.
76. Iwata, R., Ido, T., Takahashi, T. etal. (1987). Optimization of [
no-carrier-added [1-
11
C]amino acid synthesis. Int. J. Radiat. Appl. Instrum. A Appl.
11
C]HCN production and
Radiat. Isot. 38 (2): 97–102.
77. Lamb, J.F., James, R.W., and Winchell, H.S. (1971). Recoil synthesis of high specic
activity
11
C-cyanide. Int. J. Appl. Radiat. Isot. 22 (8): 475–479.
222 Handbook of Radiopharmaceuticals
78. Roeda, D., Van Zanten, B., and Crouzel, C. (1978). The production of 11C-phosgene
without added carrier. Radiochem. Radioanal. Lett. 33: 175–178.
79. Crouzel, C., Roeda, D., Berridge, M. etal. (1983).
11
C-labelled phosgene: an improved
procedure and synthesis device. Int. J. Appl. Radiat. Isot. 34 (11): 1558–1559.
80. Brinkman, G.A., Haas-Lisewska, I., Veenboer, J.T., and Lindner, L. (1978). Preparation
11
of
COCl2. Int. J. Appl. Radiat. Isot. 29 (11): 701–702.
81. Roeda, D. and Westera, G. (1981). A U.V.-induced on-line synthesis of
11
C-phosgene and the preparation of some of its derivatives. Int. J. Appl. Radiat. Isot. 32
(12): 931–932.
82. Diksic, M., Jolly, D., and Farrokhzad, S. (1982). On-line synthesis of “No-CarrierAdded” [
11
C]phosgene. Int. J. Nucl. Med. Biol. Y: 283–285.
83. Landais, P. and Crouzel, C. (1987). A new synthesis of carbon-11 labelled phosgene.
Int. J. Radiat. Appl. Instrum. A Appl. Radiat. Isot. 38 (4): 297–300.
84. Brady, F., Luthra, S.K., Tochon-Danguy, H.J. etal. (1991). Asymmetric synthesis
of a precursor for the automated radiosynthesis of S-(3′-t-Butylamino-2′Hydroxypropoxy)-benzimidazol-2-[
11
C]one (S-[11C]CGP 12177) as a preferred radioli-
gand for β-adrenergic receptors. Int. J. Radiat. Appl. Instrum. 42 (7): 621–628.
85. Link, J.M. and Krohn, K.A. (1997). A simplied production of high specic activity [
labelled phosgene,
11
COCl2. J. Labelled Compd. Radiopharm. 40 (4): 306–308.
11
86. Nishijima, K.I., Kuge, Y., Seki, K.I. etal. (2002). A simplied and improved synthesis of
11
[
C]phosgene with iron and iron (III) oxide. Nucl. Med. Biol. 29 (3): 345–350.
87. Bramoullé, Y., Roeda, D., and Dollé, F. (2010). A simplied [
11
C]phosgene synthesis.
Tetrahedron Lett. 51 (2): 313–316.
88. Ogawa, M., Takada, Y., Suzuki, H. etal. (2010). Simple and eective method for producing [
11
C]phosgene using an environmental CCl4 gas detection tube. Nucl. Med.
Biol. 37 (1): 73–76.
89. Christman, D., Crawford, E.J., Friedkin, M., and Wolf, A.P. (1972). Detection of DNA
synthesis in intact organisms with positron-emitting [methyl-
11
C]thymidine. Proc.
Natl. Acad. Sci. USA 69 (4): 988–992.
90. Berger, G., Mazière, M., Marazano, C., and Comar, D. (1978). Carbon 11 labeling of the
psychoactive drug O-methyl-bufotenine and its distribution in the animal organism.
Eur. J. Nucl. Med. 3 (2): 101–104.
91. Roeda, D. and Dollé, F. (2003). Preparation of [
11
C]formaldehyde using a silver-con-
taining ceramic catalyst. J. Labelled Compd. Radiopharm. 46 (5): 449–458.
92. Nader, M., Thobald, A., and Oberdorfer, F. (1997). Novel synthesis of [
hyde and its application in the labelling of α-(n-
11
C-Methylamino)isobutyc acid. J.
11
C]formalde-
Labelled Compd. Radiopharm. 40 (11): 730–731.
93. Slegers, G., Lambrecht, R.H., Vandewalle, T. etal. (1984). Enzymatic synthesis of C-11
formaldehyde: concise communication. J. Nucl. Med. 25 (3): 338–342.
94. Hughes, J.A. and Jay, M. (1995). Preparation of [
11
C] formaldehyde using a hollow
ber membrane bioreactor. Nucl. Med. Biol. 22 (1): 105–109.
95. Hooker, J.M., Schönberger, M., Schieferstein, H., and Fowler, J.S. (2008). A simple,
rapid method for the preparation of [
11
C]formaldehyde. Angew. Chemie Int. Ed. 47 (32):
5989–5992.
C]
223
96. Niisawa, K., Ogawa, K., Saito, J. etal. (1984). Production of no-carrier-added 11C-carbon
disulde and
11
C-hydrogen cyanide by microwave discharge. Int. J. Appl. Radiat. Isot. 35
(1): 29–33.
97. Miller, P.W. and Bender, D. (2012). [
11
C]Carbon disulde: a versatile reagent for PET
radiolabelling. Chem. Eur. J. 18 (2): 433–436.
98. Haywood, T., Kealey, S., Sánchez-Cabezas, S. etal. (2015). Carbon-11 radiolabelling
of organosulfur compounds:
11
C synthesis of the progesterone receptor agonist
tanaproget. Chem. Eur. J. 21 (25): 9034–9038.
99. Haskali, M.B. and Pike, V.W. (2017). [
11
C]Fluoroform, a breakthrough for versatile
labeling of PET radiotracer triuoromethyl groups in high molar activity. Chem. Eur.
J. 23 (34): 8156–8160.
100. Schoeps, K.-O., Halidin, C., Stone-Elander, S. etal. (1988). Preparation of
11
C-nitromethane and an example of its use as a radiolabeling precursor. J. Labelled Compd.
Radiopharm. 25 (7): 749–758.
101. Schoeps, K.-O., Stone-Elander, S., and Halldin, C. (1989). On-line synthesis of [
11
C]
nitroalkanes. Int. J. Radiat. Appl. Instrum. A Appl. Radiat. Isot. 40 (3): 261–262.
102. Crouzel, C., Amano, R., and Fournier, D. (1987). Synthesis of carbon-11 labelled diazomethane. Int. J. Radiat. Appl. Instrum. A Appl. Radiat. Isot. 38 (8): 669–670.
103. Schirrmacher, R., Lakhrissi, Y., Jolly, D. etal. (2008). Rapid in situ synthesis of [
methyl azide and its application in
11
C click-chemistry. Tetrahedron Lett. 49 (33):
11
C]
4824–4827.
104. Bordenave, T., Hazari, P.P., James, D. etal. (2013).
azide: simplied, versatile, and practical alternative access to [
11
[
C]oligonucleotides for PET imaging. Eur. J. Org. Chem. 2013 (7): 1214–1217.
105. Nader, M.W. and Oberdorfer, F. (2011). [
11
C]Lithium trimethylsilyl ynolate: a new [11C]
11
C click chemistry using [11C]methyl
11
C]nucleosides and
precursor and its application in heterocyclic synthesis. Tetrahedron Lett. 52 (18):
2309–2311.
106. Nazih, R., Blauser, J.P., Mock, B.H., and DeGrado, T.R. (2005). A facile synthesis of [
11
C]
acetylene. Appl. Radiat. Isot. 63 (3): 305–309.
107. Madsen, M.T., Hichwa, R.D., and Nickles, R.J. (1981). An investigation of
13
N-nitrous oxide and 11C-acetylene as regional cerebral blood ow agents. Phys.
11
C-methane,
Med. Biol. 26 (5): 875–882.
108. Jewett, D.M., Ehrenkaufer, R.L., and Ram, S. (1985). A captive solvent method for
rapid radiosynthesis: application to the synthesis of [1-
11
C]palmitic acid. Int. J. Appl.
Radiat. Isot. 36 (8): 672–674.
109. Leonard Watkins, G., Jewett, D.M., Keith Mulholland, G. etal. (1988). A captive solvent method for rapid N-[
11
C]methylation of secondary amides: application to the
benzodiazepine, 4′-chlorodiazepam (RO5-4864). Int. J. Radiat. Appl. Instrum. A Appl.
Radiat. Isot. 39 (5): 441–444.
110. Iwata, R., Pascali, C., Yuasa, M. etal. (1992). On-line [
methyl iodide for the automated preparation of
11
C]methylation using [11C]
11
C-radiopharmaceuticals. Int. J.
Radiat. Appl. Instrum. A Appl. Radiat. Isot. 43 (9): 1083–1088.
224 Handbook of Radiopharmaceuticals