PMID: 8944763Nov 1, 1996Paper

Role of hydrophobic substituents in the interaction of opioid Tyr-Tic dipeptide analogs with dodecylphosphocholine micelles. Molecular partitioning in model membrane systems

European Journal of Biochemistry
K A CarpenterP W Schiller

Abstract

The conformational properties of three Tyr-Tic-NH-R dipeptide analogs [where R = (CH2)2-Ph, (CH2)3-Ph or (CH2)2-cHx; Ph = phenyl; cHx = cyclohexyl and Tic = tetrahydroisoquinoline-3-carboxylic acid] have been investigated in purely aqueous solution and in the presence of fully deuterated dodecylphosphocholine micelles. H-Tyr-Tic-NH-(CH2)2-Ph is an opioid delta-agonist, whereas H-Tyr-Tic-NH-(CH2)3-Ph is a fairly potent delta-antagonist. H-Tyr-Tic-NH-(CH2)2-cHx is a less potent delta-antagonist. 1H-NMR spectra revealed that conformers containing cis and trans configurations of the Tyr-Tic peptide bond were present in all compounds in H2O and the H2O/lipid solvent. Analyses of the NMR data for the compounds in H2O indicate that in all three dipeptides the C-terminal substituent is flexible and the Tyr-side-chain adopts a trans orientation in most of the conformations. This promotes a compact Tyr-Tic structure. NOE patterns observed for the compounds in the micelle solution indicate that Tyr has an even greater tendency to assume a trans side chain configuration in the biphasic-solvent system. This feature was more pronounced in the trans conformers than in the cis conformers. Specific lipid-peptide interactions were indicated by N...Continue Reading

References

Dec 15, 1992·Proceedings of the National Academy of Sciences of the United States of America·B L KiefferC G Hirth
Dec 28, 1992·Science·C J EvansR H Edwards
Jan 1, 1989·Methods in Enzymology·L R Brown, B T Farmer
Aug 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·D F Sargent, R Schwyzer
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Citations

Oct 10, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·Pietro AmodeoPiero A Temussi
Nov 30, 2012·Biopolymers·Sara SantosMiguel A R B Castanho
Oct 14, 2004·Journal of the American Chemical Society·Cecilia BombelliStéphane Viel

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