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Silver-assisted gold-catalyzed formal synthesis of the anticoagulant Fondaparinux pentasaccharide
Communications Chemistry ( IF 5.9 ) Pub Date : 2021-02-15 , DOI: 10.1038/s42004-021-00452-y
Gulab Walke 1 , Niteshlal Kasdekar 1 , Yogesh Sutar 1 , Srinivas Hotha 1
Affiliation  

Clinically approved anti-coagulant Fondaparinux is safe since it has zero contamination problems often associated with animal based heparins. Fondaparinux is a synthetic pentasaccharide based on the antithrombin-binding domain of Heparin sulfate and contains glucosamine, glucuronic acid and iduronic acid in its sequence. Here, we show the formal synthesis of Fondaparinux pentasaccharide by performing all glycosidations in a catalytic fashion for the first time to the best of our knowledge. Designer monosaccharides were synthesized avoiding harsh reaction conditions or reagents. Further, those were subjected to reciprocal donor-acceptor selectivity studies to guide [Au]/[Ag]-catalytic glycosidations for assembling the pentasaccharide in a highly convergent [3 + 2] or [3 + 1 + 1] manner. Catalytic and mild activation during glycosidations that produce desired glycosides exclusively, scalable route to the synthesis of unnatural and expensive iduronic acid, minimal number of steps and facile purifications, shared use of functionalized building blocks and excellent process efficiency are the salient features.



中文翻译:

银辅助金催化形式合成抗凝剂磺达肝素五糖

经临床批准的抗凝血剂磺达肝素是安全的,因为它具有通常与动物肝素相关的零污染问题。Fondaparinux 是一种基于硫酸肝素抗凝血酶结合结构域的合成五糖,其序列中包含氨基葡萄糖、葡萄糖醛酸和艾杜糖醛酸。在这里,据我们所知,我们首次以催化方式进行所有糖苷化,展示了磺达肝素五糖的正式合成。设计者单糖的合成避免了苛刻的反应条件或试剂。此外,这些进行了相互供体-受体选择性研究,以指导 [Au]/[Ag]-催化糖苷化以高度收敛的 [3 + 2] 或 [3 + 1 + 1] 方式组装五糖。

更新日期:2021-02-15
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