Enhancement of the chiroptical response of α‐amino acids via N ‐substitution for molecular structure determination using vibrational circular dichroism
| Autor: | Vijay V. Raghavan, Prasad L. Polavarapu, Ernesto Santoro, Cody L. Covington |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
endocrine system
Optical Phenomena Hydrogen Nitrogen chemistry.chemical_element 010402 general chemistry Vibration 01 natural sciences Catalysis Spectral line Analytical Chemistry Drug Discovery Molecule Amino Acids Conformational isomerism Spectroscopy Pharmacology chemistry.chemical_classification Quantitative Biology::Biomolecules 010405 organic chemistry Chemistry Circular Dichroism Organic Chemistry Tryptophan Stereoisomerism 0104 chemical sciences Amino acid Crystallography Yield (chemistry) Vibrational circular dichroism |
| Zdroj: | Chirality. 32:564-578 |
| ISSN: | 1520-636X 0899-0042 |
| DOI: | 10.1002/chir.23205 |
| Popis: | The chiroptical response in the form of vibrational circular dichroism (VCD) in the midinfrared region is found to be enhanced when a hydrogen of amino group of l-tryptophan is substituted with acetyl, acryloyl, or maleyl group. The order of preference for VCD enhancement is found to be acryloyl > acetyl > maleyl group. The resulting experimental VCD spectra are also found to be satisfactorily reproduced by the quantum mechanical (QM) predicted spectra. The QM predicted spectra were simulated using the conformer populations, (a) predicted by Gibbs energies and (b) optimized to maximize the similarity between experimental and predicted VCD spectra. It is found that the conformer populations predicted by Gibbs energies do not yield the maximum possible similarity between experimental and the QM predicted spectra. This work identifies the N-substitution of α-amino acids and determining the conformer populations that best reproduce the experimental spectra as two new approaches for molecular structure determination. |
| Databáze: | OpenAIRE |
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