Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol

Wanat, Monika; Malińska, Maura; Kucia, Malgorzata; Siciński, Rafał R.; Woźniak, Krzysztof

doi:10.3390/ijms23073875

Cited by 4 publications

(1 citation statement)

References 42 publications

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“…Xylitol crystals were found to show two conformational patterns, in which φ2/φ3 = 60°/180° ( n = 33) or 180°/60° ( n = 12). It has been suggested that xylitol has two patterns of stable conformations [ 10 ]. The left- and right-handed bent conformations must be equally probable due to the symmetrical property of xylitol [ 22 ].…”

Section: Resultsmentioning

confidence: 99%

Comparative Conformational Analysis of Acyclic Sugar Alcohols Ribitol, Xylitol and d-Arabitol by Solution NMR and Molecular Dynamics Simulations

Ohno,

Manabe,

Uzawa

et al. 2024

Molecules

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Ribitol (C5H12O5) is an acyclic sugar alcohol that was recently identified in O-mannose glycan on mammalian α-dystroglycan. The conformation and dynamics of acyclic sugar alcohols such as ribitol are dependent on the stereochemistry of the hydroxyl groups; however, the dynamics are not fully understood. To gain insights into the conformation and dynamics of sugar alcohols, we carried out comparative analyses of ribitol, d-arabitol and xylitol by a crystal structure database search, solution NMR analysis and molecular dynamics (MD) simulations. The crystal structures of the sugar alcohols showed a limited number of conformations, suggesting that only certain stable conformations are prevalent among all possible conformations. The three-bond scholar coupling constants and exchange rates of hydroxyl protons were measured to obtain information on the backbone torsion angle and possible hydrogen bonding of each hydroxyl group. The 100 ns MD simulations indicate that the ribitol backbone has frequent conformational transitions with torsion angles between 180∘ and ±60∘, while d-arabitol and xylitol showed fewer conformational transitions. Taking our experimental and computational data together, it can be concluded that ribitol is more flexible than d-arabitol or xylitol, and the flexibility is at least in part defined by the configuration of the OH groups, which may form intramolecular hydrogen bonds.

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Section: Resultsmentioning

confidence: 99%

Comparative Conformational Analysis of Acyclic Sugar Alcohols Ribitol, Xylitol and d-Arabitol by Solution NMR and Molecular Dynamics Simulations

Ohno,

Manabe,

Uzawa

et al. 2024

Molecules

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Unraveling connections with artificial sweeteners and their impact on human health: A comprehensive review

Gopalakrishnan,

Balasubramanian,

Kundapur

et al. 2024

eFood

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There is a recent trend showing an uptick in the artificial sweetener's usage, particularly the nonnourishing variety. The allure of a low‐calorie choice that lets people indulge in their sweet tooths while consuming less calories overall is what motivates this. Children's food products often contain a substantial number of artificial sweeteners due to their properties that aid in moisture retention, act as fillers, and serve as bulking agents. This article provides a comprehensive overview of artificial sweeteners and influences in human wealth. Studies have linked the use of artificial sweeteners to premature birth, highlighting the teratogenic potential of these compounds, particularly in beverages. Pregnant women who incorporate nonnutritive sweeteners into their diet during pregnancy are more likely to have children with birth defects, as indicated by studies on the subject. Artificial sweeteners should not be added to food for children because studies show that eating them while a child's body is still developing might disturb the balance of gut microbiota and cause potential problems like heart disease, stroke, and cognitive decline. The ingestion of nonnourishing sweeteners has adverse effects on the fertility of both men and women. Studies indicate that exceeding the recommended daily consumption that the FDA has set for artificial sweeteners can result in conditions of infertility for both genders. Additionally, there is a connection between the onset of cancer and the use of artificial sweeteners. Presently, a considerable amount of research relies on animal models rather than human ones, creating a notable gap in research. The limitation of extensive human model studies represents a drawback in validating results. Furthermore, there is a necessity for increased research focused on advancing techniques that can minimize the adverse effects of artificial sweeteners, making them more suitable for addressing issues related to obesity and various types of diabetes.

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Chiral Resolution by Seeded Crystallization: The Case of Arabitol

Borchardt-Setter,

Yu,

Yao

et al. 2024

Crystal Growth & Design

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First demonstrated by Pasteur, chiral separation by crystallization is perhaps the simplest method to resolve a racemic mixture into pure enantiomers, but is considered inapplicable to most chiral compounds (90−95%) due to their spontaneous crystallization as a compound where the opposite enantiomers coinhabit the unit cell. Here, we demonstrate that chiral separation by crystallization can occur by seeding in a system (neat arabitol melt) that otherwise crystallizes a racemic compound. The approach helps extend chiral separation by crystallization to systems that were previously thought impossible.

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Rotamers in Crystal Structures of Xylitol, D-Arabitol and L-Arabitol

Cited by 4 publications

References 42 publications

Comparative Conformational Analysis of Acyclic Sugar Alcohols Ribitol, Xylitol and d-Arabitol by Solution NMR and Molecular Dynamics Simulations

Comparative Conformational Analysis of Acyclic Sugar Alcohols Ribitol, Xylitol and d-Arabitol by Solution NMR and Molecular Dynamics Simulations

Unraveling connections with artificial sweeteners and their impact on human health: A comprehensive review

Chiral Resolution by Seeded Crystallization: The Case of Arabitol

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