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Synthesis of α,β‐DI[ 3 H]–2–fluoro–L–histidine
Author(s) -
Takahashi Kazuyuki,
Kirk Kenneth L.,
Cohen Louis A.
Publication year - 1986
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580230102
Subject(s) - chemistry , histidine , imidazole , methanol , carbanion , enantiomer , hippuric acid , aldehyde , stereochemistry , racemization , selective reduction , medicinal chemistry , organic chemistry , catalysis , enzyme , urine , biochemistry
The potent antimetabolite, 2‐fluoro‐L‐histidine, has been synthesized from 2‐fluoroimidazole with nonexchangeable 3 H labeling in the side chain. 2‐Fluoro‐4‐iodoimidazole was N‐tritylated, was subjected to metal‐halogen exchange with n‐butyllithium, and the carbanion formylated with DMF. The imidazole‐4‐aldehyde was condensed with hippuric acid, the azlactone was solvolyzed with methanol, and the trityl group was removed by selective reduction with PtS 2 . The resultinq 2‐fluoro‐α‐benzamidoacrylic ester was reduced with tritium gas and the blocking groups were removed successively with base and with acylase I to produce the L‐enantiomer of the free amino acid analogue.