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Photocycloaddition of α,β-unsaturated-γ-lactam with ethylene. Synthesis of conformationally restricted glutamate analogs, l-2-(2-carboxycyclobutyl)glycines

✍ Scribed by Hidekazu Tsujishima; Kuniko Nakatani; Keiko Shimamoto; Yasushi Shigeri; Noboru Yumoto; Yasufumi Ohfune


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
231 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


Both (2S, 1'S,2'S)-and (2S, l'S,2'R)-isomers of 2-(2-carboxycyclobutyl)glycine (CBG-I, lb) and (CBG-III, 2b) are synthesized in a stereoselective manner via a [2+2] photocycloaddition of oc,[3unsaturated-y-lactam 3 with ethylene in acetone. The extended type of isomer lb showed a weak activity on group II metabotropic glutamate receptors (mGluR2) of rat brain.