Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 30, S-10044, Stockholm, Sweden.
Org Biomol Chem. 2011 May 7;9(9):3188-98. doi: 10.1039/c1ob05040k. Epub 2011 Mar 18.
A series of light-activatable perfluorophenylazide (PFPA)-conjugated carbohydrate structures have been synthesized and applied to glycoarray fabrication. The glycoconjugates were structurally varied with respect to anomeric attachment, S-, and O-linked carbohydrates, respectively, as well as linker structure and length. Efficient stereoselective synthetic routes were developed, leading to the formation of the PFPA-conjugated structures in good yields over few steps. The use of glycosyl thiols as donors proved especially efficient and provided the final compounds in up to 70% total yield with high anomeric purities. PFPA-based photochemistry was subsequently used to generate carbohydrate arrays on a polymeric surface, and surface plasmon resonance imaging (SPRi) was applied for evaluation of carbohydrate-protein interactions using the plant lectin Concanavalin A (Con A) as a probe. The results indicate better performance and equal efficiency of S- and O-linked structures with intermediate linker length.
已经合成了一系列可光活化的全氟苯叠氮化物（PFPA）-缀合的碳水化合物结构，并将其应用于糖基阵列的制备。糖缀合物在糖苷键的连接位置、S-和 O-连接的碳水化合物以及连接子的结构和长度方面具有结构多样性。开发了高效的立体选择性合成路线，通过少数步骤以良好的产率形成了 PFPA-缀合结构。使用糖基硫醇作为供体特别有效，并以高达 70%的总产率和高的糖基纯度提供了最终化合物。随后，基于 PFPA 的光化学被用于在聚合物表面上生成碳水化合物阵列，并应用表面等离子体共振成像（SPRi）来评估植物凝集素 Concanavalin A（Con A）作为探针的碳水化合物-蛋白质相互作用。结果表明，具有中等连接子长度的 S-和 O-连接结构具有更好的性能和相同的效率。
