Bikunin, a chondroitin sulfate (CS) proteoglycan clinically used to treat acute inflammation and sepsis, contains a CS chain with more than 20 monosaccharide units. To understand the function of the CS chain of bikunin, synthesis of long CS chains is needed. After exploring multiple glycosylation approaches and protective group chemistry, we report herein the successful generation of the longest CS chain to date (24-mer) in an excellent overall yield on a multi-mg scale. The anti-inflammatory activities of both bikunin and the synthetic 24-mer were determined, and the results demonstrate that both the glycan and the core protein are important for anti-inflammatory activities of bikunin by reducing macrophage production of proinflammatory cytokines.

中文翻译：

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Bikunin相关硫酸软骨素24-mer的化学合成和抗炎活性

Bikunin是一种临床用于治疗急性炎症和败血症的硫酸软骨素（CS）蛋白聚糖，其CS链包含20多个单糖单元。为了理解比库宁CS链的功能，需要合成长CS链。在探索了多种糖基化方法和保护基化学之后，我们在此报告了迄今为止成功的最长CS链（24-mer）的成功生成，其多毫克规模的总收率非常好。测定了比库宁和合成的24-mer的抗炎活性，结果表明，聚糖和核心蛋白均通过减少促炎细胞因子的巨噬细胞产生而对比库宁的抗炎活性很重要。