Convergent Synthesis and Anti‐Pancreatic Cancer Cell Growth Activity of a Highly Branched Heptadecasaccharide from Carthamus tinctorius
Convergent Synthesis and Anti‐Pancreatic Cancer Cell Growth Activity of a Highly Branched Heptadecasaccharide from Carthamus tinctorius
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红花高度支化十七糖的聚合合成及其抗胰腺癌细胞生长活性
DOI：
10.1002/ange.202202554
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Kan Ding
中科院分区：
文献类型：
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作者：
Chaoyu Hu;Shengjie Wu;Fei He;Deqin Cai;Zhuojia Xu;Wenjing Ma;Yating Liu;Bangguo Wei;Tiehai Li;Kan Ding
来自自然资源的生物活性多糖针对各种生物过程，并越来越多地用作药物开发的潜在靶分子。然而，具有明确结构的分支和长的复杂多糖活性结构域的可及性仍然是一个主要挑战。在此，我们描述了一种有效的第一次全合成的高度支化十七糖部分的天然生物活性半乳糖凝集素-3-靶向多糖从红花L。以及十七糖的较短片段。该方法的关键特征是光辅助会聚[6+4+7]一锅法偶联策略使得十七糖能够快速组装，由此光可去除的邻硝基苄基保护基用于在紫外辐射下原位产生用于糖基化的相应受体。生物活性测试表明，十七糖可以靶向半乳糖凝集素-3，并抑制胰腺癌细胞的生长。
Bioactive polysaccharides from natural resources target various biological processes and are increasingly used as potential target molecules for drug development. However, the accessibility of branched and long complex polysaccharide active domains with well-defined structures remains a major challenge. Herein we describe an efficient first total synthesis of a highly branched heptadecasaccharide moiety of the native bioactive galectin-3-targeting polysaccharide from Carthamus tinctorius L. as well as shorter fragments of the heptadecasaccharide. The key feature of the approach is that a photo-assisted convergent [6+4+7 one-pot coupling strategy enables rapid assembly of the heptadecasaccharide, whereby a photoremovable o-nitrobenzyl protecting group is used to generate the corresponding acceptor for glycosylation in situ upon ultraviolet radiation. Biological activity tests suggest that the heptadecasaccharide can target galectin-3 and inhibit pancreatic cancer cell growth.