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Crystallization Behavior and Crystallographic Properties of dl-Arabinose and dl-Xylose Diastereomer Sugars
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2022-01-12 , DOI: 10.1021/acs.cgd.1c01329 Bradley Tyson 1 , Christopher M Pask 2 , Neil George 1, 3 , Elena Simone 4, 5
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2022-01-12 , DOI: 10.1021/acs.cgd.1c01329 Bradley Tyson 1 , Christopher M Pask 2 , Neil George 1, 3 , Elena Simone 4, 5
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Natural sugar molecules such as xylose and arabinose exhibit sweetness profiles similar to sucrose, which makes them a valuable alternative in low-calorie foods as well as excipients or cocrystallization agents in pharmaceutical formulations. Xylose and arabinose are also chiral diastereomers that can exhibit specific crystallization behavior. In this work, the solid-state landscapes of the chiral pairs of both xylose and arabinose have been investigated to determine whether racemic compounds or conglomerates are formed. Furthermore, single crystals of xylose and arabinose have been grown and characterized by X-ray diffraction and optical microscopy to study their crystallographic properties and relate them to the crystallization behavior. Differential scanning calorimetry (DSC) measurements were used to determine the phase diagrams of the two analyzed chiral systems. The solubilities of the different solid forms of xylose and arabinose were measured in different solvent mixtures by a thermogravimetric method. An analysis was conducted to assess the main thermodynamic parameters and the activity coefficients of the compounds in solution. Finally, slurry experiments in a 50:50 w/w ethanol/water solvent have also been performed to determine the relative stability of each solid form and the kinetics of transformation in this solvent mixture. It was found that dl-arabinose crystallizes as a stable racemic compound, which transforms quickly from its constituent enantiomers when in solution; whereas d- and l-xylose molecules crystallize separately as a conglomerate.
中文翻译：
dl-阿拉伯糖和 dl-木糖非对映体糖的结晶行为和晶体学性质
木糖和阿拉伯糖等天然糖分子具有与蔗糖相似的甜味特征，这使其成为低热量食品以及药物制剂中的赋形剂或共结晶剂的有价值的替代品。木糖和阿拉伯糖也是手性非对映异构体，可以表现出特定的结晶行为。在这项工作中，研究了木糖和阿拉伯糖的手性对的固态景观，以确定是否形成外消旋化合物或聚集体。此外，木糖和阿拉伯糖的单晶已经生长并通过 X 射线衍射和光学显微镜进行表征，以研究它们的晶体学特性并将其与结晶行为联系起来。差示扫描量热法 (DSC) 测量用于确定两个分析的手性系统的相图。通过热重法测量不同固体形式的木糖和阿拉伯糖在不同溶剂混合物中的溶解度。进行分析以评估溶液中化合物的主要热力学参数和活度系数。最后，还在 50:50 w/w 乙醇/水溶剂中进行了浆料实验，以确定每种固体形式的相对稳定性以及在该溶剂混合物中的转化动力学。结果发现， dl-阿拉伯糖结晶为稳定的外消旋化合物，在溶液中时其组成的对映体迅速转变；而d-和l-木糖分子则作为聚集体分别结晶。
更新日期：2022-02-02
中文翻译：
dl-阿拉伯糖和 dl-木糖非对映体糖的结晶行为和晶体学性质
木糖和阿拉伯糖等天然糖分子具有与蔗糖相似的甜味特征，这使其成为低热量食品以及药物制剂中的赋形剂或共结晶剂的有价值的替代品。木糖和阿拉伯糖也是手性非对映异构体，可以表现出特定的结晶行为。在这项工作中，研究了木糖和阿拉伯糖的手性对的固态景观，以确定是否形成外消旋化合物或聚集体。此外，木糖和阿拉伯糖的单晶已经生长并通过 X 射线衍射和光学显微镜进行表征，以研究它们的晶体学特性并将其与结晶行为联系起来。差示扫描量热法 (DSC) 测量用于确定两个分析的手性系统的相图。通过热重法测量不同固体形式的木糖和阿拉伯糖在不同溶剂混合物中的溶解度。进行分析以评估溶液中化合物的主要热力学参数和活度系数。最后，还在 50:50 w/w 乙醇/水溶剂中进行了浆料实验，以确定每种固体形式的相对稳定性以及在该溶剂混合物中的转化动力学。结果发现， dl-阿拉伯糖结晶为稳定的外消旋化合物，在溶液中时其组成的对映体迅速转变；而d-和l-木糖分子则作为聚集体分别结晶。
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