生物素功能化透明质酸二糖的合成  

Synthesis of biotin functionalized hyaluronic acid disaccharide derivative

作　　者：孙斌 SUN Bin(College of environment and resources,Chongqing Technology and Business University,Chongqing 400067,China)

机构地区：[1]重庆工商大学环境与资源学院,重庆400067

出　　处：《化学研究与应用》2023年第3期545-551,共7页Chemical Research and Application

基　　金：重庆工商大学重点研究基金项目资助。

摘　　要：透明质酸(Hyaluronic Acid,HA)是细胞外基质的组成部分,它与细胞表面受体CD44的相互作用在许多生物事件如细胞的增殖与转移等中发挥着重要作用,由于CD44-HA的结合对于下游信号传导至关重要,能选择性地破坏HA-CD44复合物形成的化合物可以用作CD44介导的细胞事件的有用探针以及用于治疗这些事件引起的疾病的潜在新方法。为此本文报道一个有可能干预HA-CD44复合物形成的化合物生物素功能化的透明质酸二糖(HA2)类似物的合成,以全保护的氨基葡萄糖2为起始物,经过13步反应,以15%的最终收率得到生物素功能化的HA2。目标产物和关键中间体都经过核磁共振氢谱、碳谱,ESI-质谱或高分辨质谱表征。Hyaluronan(HA)is an integral component of the extracellular matrix.The interaction of HA with a cell surface receptor CD44 has been shown to play important roles in a variety biological events,such as cell proliferation and metastasis.Due to the binding of HA-CD44 is critical for for downstream signaling,compound which can selectively disrupt the formation of HA-CD44 complex can use as probe for detection of CD44 mediated cellar events as well as potential leads for novel therapeutics.Herein,the synthesis of a biotin functionalized HA disaccharide analogue for targeting the HA binding pocket of CD44 was reported.The target product was obtained starting from the fully protected aminoglucose 2 via 13 reaction steps in 15%total yield.The target product and key mediates were characterized by ^(1)H NMR and 13C NMR,ESI-MS or HRMS.

关 键 词：透明质酸 二糖 生物素 糖苷化反应 

分 类 号：O621[理学—有机化学]