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AcO
AcO
AcO
AcO
AcO
AcO
33 % HBr
O
O
NaSSO
2
Ph
Bu
4
NBr
CH
3
CN/DMF
70 °C, 20 min
OAc
Br
AcOH
18
F
18
F
98
101
NH
AcO
AcO
AcO
HN
NH
2
O
S
O
S
50 mM Tris buffer
pH 7.7, 7 % CH
3
CN
18
F
AcO
Ac
AcO
O
O
NH
HN
SO
2
S
18
F
O
NH
HN
N
103
104
O
O
COOH
SCHEME 7.23
S-S click coupling reaction between FDG and a cyclic RGD peptide.
7.5 CONCLUSION AND OUTLOOK
Click chemistry is a significant advance in the elaboration of radiotracers where time
and final product purification are important constraints. CuAAC, a fast and almost
total reaction, has attracted considerable interest in the field of radiochemistry. It
is a unique way to assemble a biomolecule and a carbohydrate either as a radioac-
tive prosthetic group or as a helpful component to modify the pharmacokinetics of
the radiotracer. This reaction gave high chemical and radiochemical yields and will
certainly find several applications in the near future of molecular imaging. If the
introduction of azide or alkyne functions on carbohydrates and nucleosides is well
documented, thanks to a large body of work performed in the last five decades, the
modification of peptide or nucleotide is still a challenging process. There is no doubt
that efforts should be done to find efficient methods of derivatization of these rather
sensitive molecules. Carbohydrates are also suitable for specific ligation methods
relying on the presence of the anomeric hydroxyl or aldehydic function. Some inter-
esting applications have been proposed but this new aspect of click chemistry must
be thoroughly studied in the near future to add new ligation methods to the toolbox
of radiochemists.
REFERENCES
1. http://www.technologyreview.com/Infotech/13060/.
2. Ametamey, S. M.; Honer, Schubiger, M. P. A.
Chem. Rev.
2008
,
108
, 1501-1516.
3. Schirrmacher, R.; Wangler, C.; Schirrmacher, E.
Mini-Rev. Org. Chem
.
2007
,
4
, 317-329.
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