Structural determinants of substrates and inhibitors: probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate.
Using an intramolecular [2 + 2] photocyclization, 2,4-methanopyrrolidine-2,4-dicarboxylate was prepared as a conformationally locked analogue of glutamate. This compound, in combination with two other pyrrolidine dicarboxylates, has been used to define the structural elements that differentiate substrate and nonsubstrate inhibitors of a high-affinity, sodium-dependent glutamate transporter.
Esslinger
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Dept. of Chemistry, University of Montana, Missoula 59812, USA.
Koch
H P
HP
Kavanaugh
M P
MP
Philips
D P
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Chamberlin
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Thompson
C M
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Bridges
R J
RJ
D018528:ATP-Binding Cassette Transporters / Q000037:antagonists & inhibitors*; D027322:Amino Acid Transport System X-AG; D000818:Animals; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D018698:Glutamic Acid / Q000031:analogs & derivatives*; D008297:Male; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis*; D051381:Rats; D017207:Rats, Sprague-Dawley
C116658:2,4-methanopyrrolidine-2,4-dicarboxylate; D018528:ATP-Binding Cassette Transporters; D027322:Amino Acid Transport System X-AG; D003998:Dicarboxylic Acids; D011759:Pyrrolidines; D018698:Glutamic Acid