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Review
. 2014:2014:214748.
doi: 10.1155/2014/214748. Epub 2014 Jun 1.

Sweetening pharmaceutical radiochemistry by (18)f-fluoroglycosylation: a short review

Simone Maschauer  1 , Olaf Prante  1
Affiliations
Review

Sweetening pharmaceutical radiochemistry by (18)f-fluoroglycosylation: a short review

Simone Maschauer et al. Biomed Res Int. 2014.

Abstract

At the time when the highly efficient [(18)F]FDG synthesis was discovered by the use of the effective precursor 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl- β -D-mannopyranose (mannose triflate) for nucleophilic (18)F-substitution, the field of PET in nuclear medicine experienced a long-term boom. Thirty years later, various strategies for chemoselective (18)F-labeling of biomolecules have been developed, trying to keep up with the emerging field of radiopharmaceutical sciences. Among the new radiochemical strategies, chemoselective (18)F-fluoroglycosylation methods aim at the sweetening of pharmaceutical radiochemistry by providing a powerful and highly valuable tool for the design of (18)F-glycoconjugates with suitable in vivo properties for PET imaging studies. This paper provides a short review (reflecting the literature not older than 8 years) on the different (18)F-fluoroglycosylation reactions that have been applied to the development of various (18)F-glycoconjugate tracers, including not only peptides, but also nonpeptidic tracers and high-molecular-weight proteins.

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Figures

Scheme 1
Scheme 1
General reaction scheme for [18F]fluoroglycosylation via CuAAC using 2-deoxy-2-[18F]fluoroglucopyranosyl azide 3, starting from the β-mannosyl azide 1.
Scheme 2
Scheme 2
General reaction scheme for 18F-fluoroglycosylation via CuAAC using 6-deoxy-6-[18F]fluoroglucopyranosyl azide 20 and 6′-deoxy-6′-[18F]fluoromaltosyl azide 22; a recent example for the alkyne is cyclic peptide c(RGDfPra), as reported by Maschauer et al. [30].
Scheme 3
Scheme 3
General reaction scheme for 18F-fluoroglycosylation via oxime formation using [18F]FDG.
Scheme 4
Scheme 4
General reaction scheme for 18F-fluoroglycosylation via oxime formation using [18F]FDR.
See this image and copyright information in PMC

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