Facile Synthesis of Sugar Nucleotides from Common Sugars by the Cascade Conversion Strategy.

Shasha Wang, Jiabin Zhang, Fangyu Wei, Wanjin Li, Liuqing Wen

Journal of the American Chemical Society 2022 Jun 08

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Sugar nucleotides are essential glycosylation donors in the carbohydrate metabolism. Naturally, most sugar nucleotides are derived from a limited number of common sugar nucleotides by de novo biosynthetic pathways, undergoing single or multiple reactions such as dehydration, epimerization, isomerization, oxidation, reduction, amination, and acetylation reactions. However, it is widely believed that such complex bioconversions are not practical for synthetic use due to the high preparation cost and great difficulties in product isolation. Therefore, most of the discovered sugar nucleotides are not readily available. Here, based on de novo biosynthesis mainly, 13 difficult-to-access sugar nucleotides were successfully prepared from two common sugars D-Man and sucrose in high yields, at a multigram scale, and without the need for tedious purification manipulations. This work demonstrated that de novo biosynthesis, although undergoing complex reactions, is also practical and cost-effective for synthetic use by employing a cascade conversion strategy.

Citation

Shasha Wang, Jiabin Zhang, Fangyu Wei, Wanjin Li, Liuqing Wen. Facile Synthesis of Sugar Nucleotides from Common Sugars by the Cascade Conversion Strategy. Journal of the American Chemical Society. 2022 Jun 08;144(22):9980-9989