Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation.
Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation.
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DOI：
10.1021/acs.jafc.1c07043
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发表时间：
2022-02
影响因子：
6.1
通讯作者：
Tianlu Li;Tong Li;Youqing Zhang;R. Schmidt;Peng Peng-Peng
中科院分区：
文献类型：
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作者：
Tianlu Li;Tong Li;Youqing Zhang;R. Schmidt;Peng Peng-Peng
茶叶香气前体苷是一种具有巨大经济价值的植物源天然产物。然而，在过去的几十年里，这些糖苷的制备在很大程度上被忽视了。在此，我们报告了一种温和，高效，可持续的化学催化程序的茶香气前体糖苷的生产。在糖苷化的研究过程中，发现催化剂在有利于不同反应途径的产物形成中起决定性作用;此外，阐明了分子筛的影响。关于这些发现，竞争原酸酯形成副反应的严重问题通过低催化剂负载量（1摩尔%）和使用5摩尔%分子筛而成功地克服，导致以经济的方式以高产率制备克规模的多种茶芳香前体β-d-吡喃葡萄糖苷和β-樱草苷。综上所述，目前的方法具有无毒和低成本催化剂的催化糖苷化作用，表现出非常有利的绿色性和可持续性，并有望工业化生产茶香气前体糖苷。
Tea aroma precursor glycosides are plant-derived natural products with great economic value. However, the preparation of these glycosides remains largely overlooked in the past decades. Herein, we report a mild, efficient, and sustainable chemocatalytic procedure for the production of tea aroma precursor glycosides. During the study of the glycosidation, the catalysts were found to be decisive in the product formation favoring different reaction pathways; in addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 Å molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical way. Taken together, the current approach features catalytic glycosidation with non-toxic and low-cost catalysts, demonstrates highly favorable greenness and sustainability, and promises industrial production of tea aroma precursor glycosides.