玻尿酸是唯一一種不含有硫酸乙醯形式，並且不存在於細胞表面的葡胺巨醣分子，它是由D型乙醯葡萄胺醣 (N-acetyl-D-glucosamine)與D型葡萄醣酸(D-glucuronic acid)以β1-3和β1-4鍵結所建構而成的雙醣體為基本單元，再重複組合而成的多醣體。玻尿酸在人體內，扮演著多樣的角色，包括了細胞的聚集、細胞周圍基質的維持、細胞與基質間訊號的傳遞、細胞的移動、血管新生和腫瘤的轉移等等。 我們利用實驗室已開發的一鍋化組合保護製程，經由一步驟的處理去合成D式葡萄硫苷醣衍生物39，之後再經兩步反應，可得醣受體36 ; 另外，也以一鍋化反應獲得化合物52，再經三步驟的處理，取得醣予體50。其後以化合物36和50，去進行醣鏈結反應，可獲得高產率且高選擇性的雙醣49，此後，再經過六步的官能基轉換，可成功合成玻尿酸雙醣分子63。 Hyaluronic acid is a linear, non-sulfated, and extracellular polymer of disaccharide repeating units which are termed as [4)-β-D-glucuronic acid-(1→3)-β-D-N-acetyl glucosamine-(1→]n. The most important biological functions of hyaluronic acid include cell-cell aggregation, cell-cell communication, cell adhesion, angiogenisis, and tumor metastasis. We tried to synthesize the p-methylphenyl-1-thio-β-D-glucose-derived 39 and D-glucosamine-derived 52 by utilizing the one-pot protection strategy which was successfully developed in our laboratory. The acceptor 36 was able to be prepared from compound 39 in two steps. On the other hand, donor 50 can be afforded by using 52 as starting material in two steps. Coupling of 36 with 50 gave the β-linked disaccharide 49 in high yield and selectivity. The target molecular 63 could be generated via the subsequent functional group transformation in 6 steps.
