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Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol
Rotamers are stereoisomers produced by rotation (twisting) about σ bonds and are often rapidly interconverting at room temperature. Xylitol—massively produced sweetener—(2R,3r,4S)-pentane-1,2,3,4,5-pentol) forms rotamers from the linear conformer by rotation of a xylitol fragment around the C2–C3 bo...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8998848/ https://www.ncbi.nlm.nih.gov/pubmed/35409233 http://dx.doi.org/10.3390/ijms23073875 |
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author | Wanat, Monika Malinska, Maura Kucia, Malgorzata Sicinski, Rafal R. Woźniak, Krzysztof |
author_facet | Wanat, Monika Malinska, Maura Kucia, Malgorzata Sicinski, Rafal R. Woźniak, Krzysztof |
author_sort | Wanat, Monika |
collection | PubMed |
description | Rotamers are stereoisomers produced by rotation (twisting) about σ bonds and are often rapidly interconverting at room temperature. Xylitol—massively produced sweetener—(2R,3r,4S)-pentane-1,2,3,4,5-pentol) forms rotamers from the linear conformer by rotation of a xylitol fragment around the C2–C3 bond (rotamer 1) or the C3–C4 bond (rotamer 2). The rotamers form two distinguishable structures. Small differences in geometry of rotamers of the main carbon chain were confirmed by theoretical calculations; however, they were beyond the capabilities of the X-ray powder diffraction technique due to the almost identical unit cell parameters. In the case of rotamers of similar compounds, the rotations occurred mostly within hydroxyl groups likewise rotations in L-arabitol and D-arabitol, which are discussed in this work. Our results, supported by theoretical calculations, showed that energetic differences are slightly higher for rotamers with rotations within hydroxyl groups instead of a carbon chain. |
format | Online Article Text |
id | pubmed-8998848 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-89988482022-04-12 Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol Wanat, Monika Malinska, Maura Kucia, Malgorzata Sicinski, Rafal R. Woźniak, Krzysztof Int J Mol Sci Article Rotamers are stereoisomers produced by rotation (twisting) about σ bonds and are often rapidly interconverting at room temperature. Xylitol—massively produced sweetener—(2R,3r,4S)-pentane-1,2,3,4,5-pentol) forms rotamers from the linear conformer by rotation of a xylitol fragment around the C2–C3 bond (rotamer 1) or the C3–C4 bond (rotamer 2). The rotamers form two distinguishable structures. Small differences in geometry of rotamers of the main carbon chain were confirmed by theoretical calculations; however, they were beyond the capabilities of the X-ray powder diffraction technique due to the almost identical unit cell parameters. In the case of rotamers of similar compounds, the rotations occurred mostly within hydroxyl groups likewise rotations in L-arabitol and D-arabitol, which are discussed in this work. Our results, supported by theoretical calculations, showed that energetic differences are slightly higher for rotamers with rotations within hydroxyl groups instead of a carbon chain. MDPI 2022-03-31 /pmc/articles/PMC8998848/ /pubmed/35409233 http://dx.doi.org/10.3390/ijms23073875 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Wanat, Monika Malinska, Maura Kucia, Malgorzata Sicinski, Rafal R. Woźniak, Krzysztof Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title | Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title_full | Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title_fullStr | Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title_full_unstemmed | Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title_short | Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol |
title_sort | rotamers in crystal structures of xylitol, d-arabitol and l-arabitol |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8998848/ https://www.ncbi.nlm.nih.gov/pubmed/35409233 http://dx.doi.org/10.3390/ijms23073875 |
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