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dc.contributor.authorEikås, Karolina Solheimsliden_GB
dc.contributor.authorBeerepoot, Maartenen_GB
dc.contributor.authorRuud, Kennethen_GB
dc.date.accessioned2022-09-13T07:20:52Z
dc.date.accessioned2022-09-15T06:47:38Z
dc.date.available2022-09-13T07:20:52Z
dc.date.available2022-09-15T06:47:38Z
dc.date.issued2022-08-05
dc.identifier.citationEikås, Beerepoot, Ruud. A Computational Protocol for Vibrational Circular Dichroism Spectra of Cyclic Oligopeptides. Journal of Physical Chemistry A. 2022en_GB
dc.identifier.urihttp://hdl.handle.net/20.500.12242/3064
dc.descriptionEikås, Karolina Solheimslid; Beerepoot, Maarten; Ruud, Kenneth. A Computational Protocol for Vibrational Circular Dichroism Spectra of Cyclic Oligopeptides. Journal of Physical Chemistry A 2022en_GB
dc.description.abstractCyclic peptides are a promising class of compounds for next-generation antibiotics as they may provide new ways of limiting antibiotic resistance development. Although their cyclic structure will introduce some rigidity, their conformational space is large and they usually have multiple chiral centers that give rise to a wide range of possible stereoisomers. Chiroptical spectroscopies such as vibrational circular dichroism (VCD) are used to assign stereochemistry and discriminate enantiomers of chiral molecules, often in combination with electronic structure methods. The reliable determination of the absolute configuration of cyclic peptides will require robust computational methods than can identify all significant conformers and their relative population and reliably assign their stereochemistry from their chiroptical spectra by comparison with ab initio calculated spectra. We here present a computational protocol for the accurate calculation of the VCD spectra of a series of flexible cyclic oligopeptides. The protocol builds on the Conformer-Rotamer Ensemble Sampling Tool (CREST) developed by Grimme and co-workers ( Phys. Chem. Chem. Phys. 2020, 22, 7169−7192 and J. Chem. Theory. Comput. 2019, 15, 2847–2862) in combination with postoptimizations using B3LYP and moderately sized basis sets. Our recommended computational protocol for the computation of VCD spectra of cyclic oligopeptides consists of three steps: (1) conformational sampling with CREST and tight-binding density functional theory (xTB); (2) energy ranking based on single-point energy calculations as well as geometry optimization and VCD calculations of conformers that are within 2.5 kcal/mol of the most stable conformer using B3LYP/6-31+G*/CPCM; and (3) VCD spectra generation based on Boltzmann weighting with Gibbs free energies. Our protocol provides a feasible basis for generating VCD spectra also for larger cyclic peptides of biological/pharmaceutical interest and can thus be used to investigate promising compounds for next-generation antibiotics.en_GB
dc.language.isoenen_GB
dc.subjectMolekyleren_GB
dc.subjectEnergien_GB
dc.titleA Computational Protocol for Vibrational Circular Dichroism Spectra of Cyclic Oligopeptidesen_GB
dc.date.updated2022-09-13T07:20:52Z
dc.identifier.cristinID2049453
dc.identifier.doi10.1021/acs.jpca.2c02953
dc.source.issn1089-5639
dc.source.issn1520-5215
dc.type.documentJournal article
dc.relation.journalJournal of Physical Chemistry A


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