[Synthesis and determination for enantiomeric purity of 6-fluoro-L-DOPA].
OBJECTIVE
To study the synthesis and determination for enantiomeric purity of 6-fluoro-L-3, 4-dihydroxyphenylalanine (6-fluoro-L-DOPA, 6-FDOPA).


METHODS
2-(2-Fluoro-4, 5-dimethoxybenzyl)-N-(diphenylmethylene) glycine tert-butyl ester (8), a new compound, was synthesized from the starting material nitroveratraldehyde via the nucleophilic displacement, reductive iodination, and chiral catalytic phase-transfer alkylation, and 6-FDOPA was prepared from hydrolysis of 8. The enantiomeric purity of 6-FDOPA was determined by HPLC method using a chiral mobil phase and reversed-phase C18 column.


RESULTS
The total time of synthesis was less than 90 min, the overall chemical yield from potassium fluoride was about 33%, and the enantiomeric purity was above 95%.


CONCLUSIONS
Large scale production of 6-FDOPA and automatic synthesis of 6-[18F]fluoro-L-DOPA with excellent chemical and entiomeric purity are available. The practical technique was provided for the radiochemical synthesis and entiomeric purity of 6-[18F]fluoro-L-DOPA.
Tang
G H
GH
Radiopharmaceutical Research Centre, Shanghai Institute of Nuclear Research, Chinese Academy of Sciences, Shanghai 201800, China. tghtgh@china.com
Zhang
L
L
Tang
X L
XL
Wang
Y X
YX
Yin
D Z
DZ
D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D013237:Stereoisomerism
D005462:Fluorine Radioisotopes; C043437:fluorodopa F 18; D004295:Dihydroxyphenylalanine