AI Article Synopsis
- Rotamers are stereoisomers formed by rotating around σ bonds, and they can quickly interchange, especially at room temperature.
- Xylitol, a widely used sweetener, can exist in different rotamer forms due to rotation at specific carbon bonds, resulting in distinguishable structures.
- Theoretical calculations revealed that the geometry differences in these rotamers, particularly those involving hydroxyl group rotations, are more significant than those involving the carbon chain but are challenging to observe with X-ray powder diffraction.
Article Abstract
Rotamers are stereoisomers produced by rotation (twisting) about σ bonds and are often rapidly interconverting at room temperature. Xylitol-massively produced sweetener-(2,3,4)-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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8998848 | PMC |
| http://dx.doi.org/10.3390/ijms23073875 | DOI Listing |
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