The prebiotic origin of polysaccharides, the largest class of biopolymers by mass in extant biology, has seldom been investigated experimentally. Herein, we report on the acid-catalyzed condensation of aqueous solutions of glucose, a model monosaccharide, under plausible prebiotic conditions employing a wet-dry (night-day) protocol with 0.01 M HCl at 50 °C. This protocol leads to the formation of oligosaccharides containing up to eight monomeric units identified by high resolution mass spectrometry. The regio- and stereochemistry of the oligomeric acetal linkages, as well as the quantitative analysis of glucose conversion, are elucidated by combining 1H, 13C and 2D NMR spectroscopy. Ten out of eleven possible acetal linkages, including α- and β- anomers, have been identified with the α- and β- 1,6-acetals being the dominant linkages observed. In addition, the acid-catalyzed oligomerization of several glucose disaccharides such as cellobiose, maltose, and gentiobiose are presented along with an accompanying comparison with the corresponding oligomerization of glucose.

中文翻译：

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在合理的益生元条件下葡萄糖的寡聚化。


多糖是现存生物学中质量最大的一类生物聚合物，其益生元起源很少经过实验研究。在此，我们报告了葡萄糖（一种模型单糖）水溶液在合理的益生元条件下，采用湿-干（夜间-白天）方案，在 50 °C 下使用 0.01 M HCl 进行酸催化缩合。该方案导致形成含有多达八个经高分辨率质谱鉴定的单体单元的寡糖。通过结合 1H、13C 和 2D NMR 光谱，阐明了低聚缩醛键的区域化学和立体化学，以及葡萄糖转化的定量分析。已鉴定出十一种可能的缩醛键中的十种，包括 α- 和 β- 异头物，其中 α- 和 β- 1,6-缩醛是观察到的主要键。此外，还介绍了几种葡萄糖二糖（例如纤维二糖、麦芽糖和龙胆二糖）的酸催化低聚反应，并与相应的葡萄糖低聚反应进行了比较。