Synthesis of Macrocyclic Analogues of the Neuroprotective Agent Glycyl-L-Prolyl-L-Glutamic acid (GPE)

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dc.contributor.author Harris, Paul en
dc.contributor.author Brimble, Margaret en
dc.date.accessioned 2011-09-19T23:11:53Z en
dc.date.issued 2006 en
dc.identifier.citation Org Biomol Chem 4(14):2696-2709 21 Jul 2006 en
dc.identifier.issn 1477-0520 en
dc.identifier.uri http://hdl.handle.net/2292/8188 en
dc.description.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. en
dc.language EN en
dc.publisher ROYAL SOC CHEMISTRY en
dc.relation.ispartofseries Organic & Biomolecular Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/1477-0520/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject RING-CLOSING METATHESIS en
dc.subject N-TERMINAL TRIPEPTIDE en
dc.subject GLYCINE-PROLINE-GLUTAMATE en
dc.subject GROWTH-FACTOR-I en
dc.subject BICYCLIC LACTAM PEPTIDOMIMETICS en
dc.subject AMINO-ACIDS en
dc.subject STEREOSELECTIVE-SYNTHESIS en
dc.subject OLEFIN METATHESIS en
dc.subject GLU GPE en
dc.subject IGF-I en
dc.title Synthesis of Macrocyclic Analogues of the Neuroprotective Agent Glycyl-L-Prolyl-L-Glutamic acid (GPE) en
dc.type Journal Article en
dc.identifier.doi 10.1039/b605293b en
pubs.issue 14 en
pubs.begin-page 2696 en
pubs.volume 4 en
dc.rights.holder Copyright: 2006 The Royal Society of Chemistry en
dc.identifier.pmid 16826294 en
pubs.end-page 2709 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 69532 en
pubs.org-id Science en
pubs.org-id Biological Sciences en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en
pubs.dimensions-id 16826294 en


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