Synthesis and neuroprotective activity of analogues of glycyl-L-prolyl-L-glutamic acid (GPE) modified at the alpha-carboxylic acid.
The synthesis of nine GPE* analogues, wherein the alpha-carboxylic acid group of glutamic acid has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline 2 with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE.
Trotter
Nicholas S
NS
Neuren Pharmaceuticals Medicinal Chemistry Group, Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland 1000, New Zealand.
Brimble
Margaret A
MA
Harris
Paul W R
PW
Callis
David J
DJ
Sieg
Frank
F
D000818:Animals; D002478:Cells, Cultured; D003342:Corpus Striatum / Q000166:cytology; D005260:Female; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008956:Models, Chemical; D015394:Molecular Structure; D009474:Neurons / Q000187:drug effects; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D019319:Okadaic Acid / Q000037:antagonists & inhibitors; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar
D018696:Neuroprotective Agents; D009842:Oligopeptides; D019319:Okadaic Acid; D018698:Glutamic Acid; C062053:glycyl-prolyl-glutamic acid