Conformational and Chiroptical Properties of Salicylamide-Based Peptidomimetics

Autor: Ivan Raich, Karel Pauk, Ales Imramovsky, Josef Jampílek
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Symmetry, Vol 16, Iss 2, p 138 (2024)
Druh dokumentu: article
ISSN: 16020138
2073-8994
DOI: 10.3390/sym16020138
Popis: Optical rotation (OR), the most frequently used chiroptical method, is used for the characterization of newly synthesized or isolated compounds. Computational predictions of OR are, however, mainly used for the determination of the absolute configurations of chiral compounds, but they may also be used for the verification of conformational analysis results if the experimental values are known. Our computational study deals with the conformational analysis of flexible salicylamide-based peptidomimetics, starting with a conformation search, then a low-level ab initio preoptimization of the hundreds of conformations found, and, finally, a higher-level DFT optimization. For the resulting minima structures, Boltzmann populations were calculated, followed by OR calculations for all the populated conformers using the DFT method with various basis sets with diffuse functions. Weighted averages of the ORs were compared with experimental values, and the agreement, which ranged from excellent to moderate for various compounds, served as a verification of the conformational analysis results.
Databáze: Directory of Open Access Journals
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