A series of 2-O-trifluoromethylsulfonyl-d-mannopyranosides as precursors for concomitant 18F-labeling and glycosylation by click chemistry

Markierung und Glycosylierung von Peptiden mithilfe der Klick‐Chemie: ein allgemeiner Ansatz zur Synthese von 18F‐Glycopeptiden, leistungsstarken Tracern für die Positronenemissionstomographie

“…Die Erhaltung der b-anomeren Konfiguration des Glycosylrestes von FGlc-NT1 wurde 19 F-NMR-spektroskopisch nachgewiesen. [15] Unseren Liganden-Bindungsexperimenten zufolge waren die glycosylierten NTR-1-Liganden nahezu äquipotent wie die entsprechenden nichtglycosylierten Derivate (Tabelle 1 [15] hergestellt, der sich die basische Hydrolyse mit NaOH anschloss (Schema 1). Danach erfolgte im selben Reaktionsgefäß in einer Mischung aus phosphatgepufferter Salzlösung (PBS) und Ethanol (10:1) bei 60 8C die Glycosylierung, die nur 100 mg des Alkin-haltigen Peptids in einem Gesamtvolumen von 500 mL benötigt.…”

Sweetening Pharmaceutical Radiochemistry by18F-Fluoroglycosylation: A Short Review

“…The synthesis of the 18 F-fluoroglycosylating agent 3,4,6-tri- O -acetyl-2-deoxy-2-[ 18 F]fluoroglucopyranosyl azide ( 3 ) was achieved by the 18 F-labeling of the precursor 3,4,6-tri- O -acetyl-2- O -trifluoromethanesulfonyl- β -D-mannopyranosyl azide ( 1 ) in high radiochemical yields (RCY) as described by Maschauer and Prante (Scheme 1) [20]. Very similar to the well-known [ 18 F]FDG synthesis, the yield of this radiochemical reaction relies mainly on the chemical purity of the labeling precursor.…”

“…Therefore, our group envisaged the appropriate idea to develop a click chemistry-based 18 F-fluoroglycosylation method to provide a general approach to the radiosynthesis of 18 F-labeled glycoconjugates as effective imaging agents for PET [19, 20]. …”

“…In 2009, we reported the synthesis of a series of “clickable” mannosides and showed their potential as 18 F-labeling precursors [20], which has been the starting point of a number of publications by others reporting on various 18 F-glycoconjugates as new PET tracers.…”

Recent Developments in Neoglycopeptide Synthesis

“…Subsequent reductive amination with Boc-Lys-OH afforded the sialic acid-containing neoglycoside in 71% yield. F-labeled glycosides have also been synthesized from 18 F-labeled mannosyl azide precursors using the copper sulfate/ascorbate catalyst system [97].…”