In this study, taking into account both the l-d and cis-trans isomerisms, a comprehensive structural characterization and a comparative conformational analysis were performed on the 32 stereoisomeric forms of opioid tetrapeptide, endomorphin-2. For all stereoisomers, the Φ-Ψ and χ conformational spaces were explored, in the course of which the conformational distributions, as well as the rotamer states of aromatic side chains were characterized in detail. Furthermore, the typical β- and γ-turn structures, as well as the characteristic intramolecular interactions (i.e., H-bonds, aromatic-aromatic and proline-aromatic interplays) were determined. The afore-mentioned structural and conformational features identified for each stereoisomeric form were compared with one another, considering all 32 stereoisomers. The results obtained from this comparative study indicated that both similarities and dissimilarities could be observed between the stereoisomeric forms, with regard to their structural and conformational properties. This theoretical work supplied several valuable observations concerning the effects of both l-d and cis-trans isomerisms on the three-dimensional structure of parent peptide and its stereoisomers. Nevertheless, in the course of this structural investigation, it was clarified how the structural and conformational features of stereoisomeric forms differed from one another. © 2011 John Wiley & Sons A/S.
CITATION STYLE
Leitgeb, B. (2012). Conformational Similarities and Dissimilarities Between the Stereoisomeric Forms of Endomorphin-2. Chemical Biology and Drug Design, 79(3), 313–325. https://doi.org/10.1111/j.1747-0285.2011.01275.x
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