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Synthesis of (2S,2′R,3′R)‐2‐(1′‐[ 3 H],2′,3′‐dicarboxylcyclopropyl)‐glycine ([ 3 H]‐DCG‐IV)
Author(s) -
Wichmann Jürgen,
Huguenin Philipp,
Adam Geo
Publication year - 2000
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/(sici)1099-1344(200001)43:1<1::aid-jlcr285>3.0.co;2-n
Subject(s) - chemistry , glycine , radioligand , stereochemistry , tritium , agonist , aldehyde , chemical synthesis , metabotropic glutamate receptor , amino acid , receptor , organic chemistry , biochemistry , in vitro , physics , nuclear physics , catalysis
The conformationally restricted analog of L‐glutamic acid (L‐Glu, 1 ) (2S,2′R,3′R)‐2‐(2′,3′‐dicarboxylcyclopropyl)‐glycine (DCG‐IV, 2 ) is a potent group II mGluR agonist. In order to study the distribution of group II mGluRs in the brain and to establish a radioligand binding assay we have developed a synthesis of [ 3 H]‐DCG‐IV ( 2a ). The key intermediate, α‐bromo aldehyde 7 , was prepared in four steps starting from (−)‐Fiest's acid ( 3 ). The incorporation of tritium was performed by reaction of 7 with tri‐n‐butyltin tritide to give 8 , which was transformed in two steps into 2a . Copyright © 2000 John Wiley & Sons, Ltd.