Naslov
Synthesis of stereo (R and S) and geometric (E and Z) isomers of [F-18]fluoro-beta-fluoromethylene-m-tyrosine derivatives : in vivo probes of central dopaminergic function

Autori
Laćan, Goran ; Satyamurthy, N. ; Barrio, Jorge R.

Izvornik
Nuclear medicine and biology (0969-8051) 26 (1999), 4; 359-363

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
dopaminergic function; monoamine oxidase inhibitor; fluorination; PET; beta-fluoromethylene-m-tyrosine; fluoromethylene-m-tyrosine; enzyme inactivator; regioselective radiofluorodestannylation; monoamine-oxidase; inhibition

Sažetak
Fluorination of pure R and S enantiomers of (E)-beta-fluoromethylene-m-tyrosine [(E)-FMMT] and its racemic geometric isomer, (Z)-beta-fluoromethylene m-tyrosine [(Z)-FMMT] with [F-18]acetyl hypofluorite ([F-18]AcOF) gave a mixture of aromatic ring fluorinated products and a pair of diastereomeric products of addition across the exocyclic double bond. Semipreparative high performance liquid chromatography (HPLC) enabled a complete separation and isolation of these products, namely, 6-[F-18]fluoro, 2-[F-18]fluoro, and 2,6-[F-18]difluoro (E)-FMMT and (Z)-FMMT derivatives, No attempt was made to isolate the individual components of the addition product. Pure racemic 4-[F-18]fluoro-(E)-beta-fluoromethylene-m-tyrosine was also synthesized from a substituted (E)-FMMT precursor involving a fluorodestannylation reaction with [F-18]F-2. The availability of stereo (R and S) isomers of 6-[F-18]fluoro and 2-[F-18]fluoro (E)-FMMT and those of the racemic (Z)-FMMT along with 4-[F-18]fluoro-(E)-beta-fluoromethylene-m-tyrosine would now enable a systematic investigation of the central monoamine oxidase/aromatic amino acid decarboxylase enzyme system with positron emission tomography.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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