Absolute configuration of (+)-alpha-methyl-4-carboxyphenylglycine (MCPG), a metabotropic glutamate receptor antagonist.
The title compound, (+)-MCPG [(+)-alpha-(4-carboxyphenyl)-alpha-methylglycine, C10H11NO4], is an antagonist at certain subtypes of metabotropic glutamate (mGlu) receptors. (+)-MCPG has gained widespread acceptance as a tool for probing the physiological role of mGlu receptors in the central nervous system. As a result, mGlu receptors are now known to be involved in processes connected with learning and memory, modulation of synaptic transmission and the transmission of pain responses. (+)-MCPG crystallized in its zwitterionic form. Its absolute configuration was assigned as S from X-ray diffraction data collected at 150 K. The refined Flack parameter is consistent with this assignment, although the large e.s.d. associated with it introduces some ambiguity.
Wilson
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Department of Chemistry, University of Durham, England. claire@kemi.aau.dk
Howard
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Jane
D E
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Sunter
D C
DC
Watkins
J C
JC
D001565:Benzoates / Q000737:chemistry*; D003460:Crystallization; D018691:Excitatory Amino Acid Antagonists / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D014961:X-Ray Diffraction
D001565:Benzoates; D018691:Excitatory Amino Acid Antagonists; C079694:alpha-methyl-4-carboxyphenylglycine; D005998:Glycine