https://scholars.lib.ntu.edu.tw/handle/123456789/641329
標題: | Toward an Improved Triterpene 3-O-Glucuronidation: The Systematic Determination of the Relative Reactivities of Glucuronyl Donors and Acceptors | 作者: | Lai, Yen-Hsun Chou, Yu-Ting Lin, You-Yu Wang, Yi-Chi Cao, Jing-Xiu PI-HUI LIANG |
公開日期: | 21-七月-2023 | 卷: | 88 | 期: | 14 | 起(迄)頁: | 9946 | 來源出版物: | The Journal of organic chemistry | 摘要: | 3-O-β-Glucuronide triterpenes are plant-derived compounds. Some of them have been used as herbal medicine and in pharmaceuticals, such as chikusetsu saponins and Quillaja saponins. However, the demand for these materials has remained largely a challenge owing to their natural scarcity and low-yielding purification process. Therefore, a chemical triterpene 3-O-glucuronidation was conducted in this study to alleviate the surging demand on natural source. Various glucuronyl imidate donors and oleanane-type triterpene acceptors were synthesized, and the relative reactivity values (RRV) and acceptor nucleophilic constants (Aka) were systematically measured to study their influence on glucuronidation yield. As a result, applying donors in higher RRV value generally improved the production of 3-O-glucuronide triterpenes. Meanwhile, a bulky pivaloyl group was an ideal 2-O-protection to provide β-selectivity and prevented side reactions, including orthoester formation and acyl-transfer reaction. Collectively, a positive correlation was observed between reactive donors/acceptors and improved glucuronidation yields. These findings offered insights on the influence of donors' and acceptors' reactivities on 3-O-β-glucuronide triterpenes synthesis, and this knowledge would help to access saponins of interest to address future needs. |
URI: | https://scholars.lib.ntu.edu.tw/handle/123456789/641329 | ISSN: | 00223263 | DOI: | 10.1021/acs.joc.3c00709 |
顯示於: | 藥學系 |
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