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Issue 14, 2006
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Synthesis of macrocyclic analogues of the neuroprotective agentglycyl-l-prolyl-l-glutamic acid (GPE)

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Abstract

The syntheses of seven macrocyclic analogues of the neuroprotective tripeptide glycyl-L-prolyl-L-glutamic acid (GPE) 1 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.

Graphical abstract: Synthesis of macrocyclic analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)

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Article information


Submitted
12 Apr 2006
Accepted
10 May 2006
First published
01 Jun 2006

Org. Biomol. Chem., 2006,4, 2696-2709
Article type
Paper

Synthesis of macrocyclic analogues of the neuroprotective agent glycyl-L-prolyl-L-glutamic acid (GPE)

P. W. R. Harris and M. A. Brimble, Org. Biomol. Chem., 2006, 4, 2696 DOI: 10.1039/B605293B

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