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

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...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 61; no. 42; pp. 10018 - 10035
Main Authors Harris, Paul W.R., Brimble, Margaret A., Muir, Victoria J., Lai, Michelle Y.H., Trotter, Nicholas S., Callis, David J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.10.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Neuroprotective
Peptide
Peptidomimetic
Physical Sciences
Proline
Science & Technology
Proline
Neuroprotective
Peptidomimetic
Peptide
CONVENIENT SYNTHESIS
peptide
IGF-I
GLU GPE
neuroprotective
peptidomimetic
N-TERMINAL TRIPEPTIDE
proline
PSEUDO-PROLINES
CIS-TRANS ISOMERIZATION
AMINO-ACIDS
HYPOXIC-ISCHEMIC INJURY
PEPTIDE-SYNTHESIS
GROWTH-FACTOR-I
Online AccessGet full text

Cover

More Information
Summary: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-CH 2 group with sulfur and/or incorporation of two methyl groups at C-5. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.08.026