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Automated Synthesis of (rac)-, (R)-, and (S)-[ 18 F]Epifluorohydrin and Their Application for Developing PET Radiotracers Containing a 3-[ 18 F]Fluoro-2-hydroxypropyl Moiety

Automated Synthesis of (rac)-, (R)-, and (S)-[ 18 F]Epifluorohydrin and Their Application for Developing PET Radiotracers Containing a 3-[ 18 F]Fluoro-2-hydroxypropyl Moiety

Masayuki Fujinaga, Takayuki Ohkubo, Tomoteru Yamasaki, Yiding Zhang, Wakana Mori, Masayuki Hanyu, Katsushi Kumata, Akiko Hatori, Lin Xie, Nobuki Nengaki, Ming-Rong Zhang

ChemMedChem. 2018 Aug 20;13(16):1723-1731.

PMID: 30043406

Abstract:

To introduce the 3-[18 F]fluoro-2-hydroxypropyl moiety into positron emission tomography (PET) radiotracers, we performed automated synthesis of (rac)-, (R)-, and (S)-[18 F]epifluorohydrin ([18 F]1) by nucleophilic displacement of (rac)-, (R)-, or (S)-glycidyl tosylate with 18 F- and purification by distillation. The ring-opening reaction of (R)- or (S)-[18 F]1 with phenol precursors gave enantioenriched [18 F]fluoroalkylated products without racemisation. We then synthesised (rac)-, (R)-, and (S)- 2-{5-[4-(3-[18 F]fluoro-2-hydroxypropoxy)phenyl]-2-oxobenzo[d]oxazol-3(2H)-yl}-N-methyl-N-phenylacetamide ([18 F]6) as novel radiotracers for the PET imaging of translocator protein (18 kDa) and showed that (R)- and (S)-[18 F]6 had different radioactivity uptake in mouse bone and liver. Thus, (rac)-, (R)-, and (S)-[18 F]1 are effective radiolabelling reagents and can be used to develop PET radiotracers by examining the effects of chirality on their in vitro binding affinities and in vivo behaviour.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP503093	Epifluorohydrin		503-09-3	Price

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