Synthesis of macrocyclic analogues of the neuroprotective agent glycyl-L-prolyl-L-glutamic acid (GPE).
The syntheses of seven macrocyclic analogues of the neuroprotective tripeptide glycyl-L-prolyl-L-glutamic acid (GPE) are described. Macrocycles 6 and 7 mimic the cis conformer of GPE whereas macrocycles 2-5, 8, and 9 mimic the trans conformer of GPE. The macrocyclic peptides of well-defined geometry were prepared via Grubbs ring closing metathesis of an appropriate diene precursor. In turn each of the diene precursors were prepared from the readily available allyl-substituted amino acid building blocks 12, 13, 14, 27, 36 and 51.
Harris
Paul W R
PW
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.
Brimble
Margaret A
MA
D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D018696:Neuroprotective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D047028:Macrocyclic Compounds; D018696:Neuroprotective Agents; D009842:Oligopeptides; C062053:glycyl-prolyl-glutamic acid