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Utility of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[18F]fluoro-glucopyranoside for no-carrier-added 18F-glycosylation of amino acids

✍ Scribed by Simone Maschauer; Monika Pischetsrieder; Torsten Kuwert; Olaf Prante

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
219 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A radiochemical method for the ^18^F‐glycosylation of amino acid side chains was developed starting from peracetylated 2‐deoxy‐2‐[^18^F]fluoroglucopyranoside (TA‐[^18^F]FDG). O‐(2‐deoxy‐2‐[^18^F]fluoro‐D‐glucopyranosyl)‐L‐serine and the corresponding threonyl compound were obtained in a radiochemical yield of 25% and 12% (related to [^18^F]fluoride), respectively, after Zemplén deprotection within a total reaction time of 90 min. The anomeric configuration of the corresponding ^19^F‐substituted compounds revealed preferential α‐stereoselectivity. The ^18^F‐glycosylation method using TA‐[^18^F]FDG is compatible with the short half‐life of fluorine‐18 and combines glycosylation and ^18^F‐labelling of a target compound within a single reaction step. TA‐[^18^F]FDG is a promising ^18^F‐labelled prosthetic group and could be adapted to ^18^F‐labelling of bioactive peptides to study their pharmacokinetics using positron emission tomography (PET). Copyright © 2005 John Wiley & Sons, Ltd.

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