Abstract
The asymmetric synthesis of (2R,1'S,2'R, 3'S)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCG-13), a trisubstituted carboxycyclopropylglycine endowed with unusual stereochemical features, is described. Preliminary biological evaluation demonstrates PCCG-13 as a very potent and selective competitive antagonist for the novel class of metabotropic glutamate (mGlu) receptors coupled to the activity of phospholipase D (PLD). PCCG-13 is therefore a useful tool for the exploration of the physiopathological role of this novel class of receptors.
MeSH terms
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Animals
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Cycloleucine / analogs & derivatives
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Cycloleucine / pharmacology
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Cyclopropanes / chemical synthesis*
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Cyclopropanes / chemistry
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Cyclopropanes / pharmacology
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Glycerophospholipids / biosynthesis
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Glycine / analogs & derivatives*
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Glycine / chemical synthesis
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Glycine / chemistry
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Glycine / pharmacology
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Hippocampus / drug effects
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Hippocampus / metabolism
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In Vitro Techniques
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Phospholipase D / metabolism*
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Rats
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Receptors, Metabotropic Glutamate / antagonists & inhibitors*
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Receptors, Metabotropic Glutamate / metabolism
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Stereoisomerism
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Type C Phospholipases / metabolism
Substances
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2-(2'-carboxy-3'-phenylcyclopropyl)glycine
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Cyclopropanes
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Glycerophospholipids
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Receptors, Metabotropic Glutamate
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phosphatidylethanol
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Cycloleucine
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1-amino-1,3-dicarboxycyclopentane
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Type C Phospholipases
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Phospholipase D
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Glycine