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Conformational analysis of endomorphin-2 analogs with phenylalanine mimics by NMR and molecular modeling
- Source :
-
Bioorganic & Medicinal Chemistry . May2007, Vol. 15 Issue 10, p3539-3547. 9p. - Publication Year :
- 2007
-
Abstract
- Abstract: We investigated a series of conformations of endomorphin-2 (EM-2) analogs substituted by phenylglycine (Phg) and homophenylalanine (Hfe) in the position 3 or 4 by two-dimensional 1H NMR spectroscopy and molecular modeling. Evaluating the aromatic interactions and the dihedral angles in these phenylalanine mimics, we have observed that the conformations in trans isomer have varied from extended to folded as bioactivity decreases. It is suggested that the flexibility of aromatic side chain affects the backbone of EM-2 to adopt folded structures, which may block the ligands in binding to μ-opioid receptor. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 09680896
- Volume :
- 15
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Bioorganic & Medicinal Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24610988
- Full Text :
- https://doi.org/10.1016/j.bmc.2007.02.050