A modular click approach to glycosylated polymeric beads:: Design, synthesis and preliminary lectin, recognition studies
A modular click approach to glycosylated polymeric beads:: Design, synthesis and preliminary lectin, recognition studies
复制标题
DOI：
10.1021/ma071362v
复制
发表时间：
2007-10-16
期刊：
影响因子：
5.5
通讯作者：
Haddleton, David M.
中科院分区：
文献类型：
--
作者：
Chen, Gaojian;Tao, Lei;Haddleton, David M.
描述了一系列碳水化合物衍生物共价固定到聚合物树脂珠上。使用铜催化的 Huisgen [2 + 3] 环加成（通常称为点击化学）将含甘露糖的叠氮化物接枝到互补功能化的炔表面，即 (a) Wang 树脂或 (b) 由可点击的炔聚合物松散外壳和 Wang 树脂内核组成的 Rasta 颗粒。对于第二种方法，首先将 Wang 树脂珠转化为固定化活性自由基聚合引发剂，随后聚合三甲基硅烷基保护的甲基丙烯酸炔丙酯，然后用 TBAF 脱保护，得到所需的聚炔可点击支架。然后将适当的（x-吡喃甘露糖苷叠氮化物）点击到珠子上，得到甘露糖功能化的 Rasta 树脂。IR、凝胶相 H-1 NMR 和元素分析已用于表征改性树脂。随后使用荧光素标记的刀豆球蛋白 A (Con A)（一种结合某些含甘露糖分子的凝集素）测试这些 D-甘露糖修饰颗粒的结合能力。初步结果表明这项工作中提出的新型糖杂化材料能够有效识别甘露糖结合模型凝集素，例如Con A，为其在亲和层析、传感器和其他蛋白质识别/分离领域的潜在应用开辟了道路。
Covalent immobilization of a range of carbohydrate derivatives onto polymeric resin beads is described. Copper-catalyzed Huisgen [2 + 3] cycloaddition (often termed click chemistry) was used to graft mannose-containing azides to complementarily functionalized alkyne surfaces, namely (a) Wang resin or (b) Rasta particles consisting of a clickable alkyne polymer loose outer shell and a Wang resin inner core. For the second approach, Wang resin beads were first converted into immobilized living radical polymerization initiators with subsequent polymerization of trimethylsilanyl-protected propargyl methacrylate followed by deprotection with TBAF to yield the desired polyalkyne clickable scaffold. The appropriate (x-mannopyranoside azide was then clicked onto the bead to give a mannose functionalized Rasta resin. IR, gel-phase H-1 NMR, and elemental analysis have been used to characterize the modified resins. The binding abilities of these D-mannose-modified particles were subsequently tested using fluorescein-labeled Concanavalin A (Con A), a lectin that binds certain mannose-containing molecules. Preliminary results indicated that the novel glyco-hybrid materials presented in this work are able to efficiently recognize mannose-binding model lectins such as Con A, opening the way for their potential application in affinity chromatography, sensors, and other protein recognition/separation fields.