Tetrahedron

Synthesis of proline-modified analogues of the neuroprotective agent glycyl-l-prolyl-glutamic acid (GPE)

PWR Harris, MA Brimble, VJ Muir, MYH Lai, NS Trotter…

Index: Harris, Paul W.R.; Brimble, Margaret A.; Muir, Victoria J.; Lai, Michelle Y.H.; Trotter, Nicholas S.; Callis, David J. Tetrahedron, 2005 , vol. 61, # 42 p. 10018 - 10035

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Citation Number: 32

Abstract

The synthesis of ten proline-modified analogues of the neuroprotective tripeptide GPE is described. Five of the analogues incorporate a proline residue with a hydrophobic group at C-2 and two further analogues have this side chain locked into a spirolactam ring system. The pyrrolidine ring was also modified by replacing the γ-CH2 group with sulfur and/or incorporation of two methyl groups at C-5.