Fukuhara Gaku, Sasaki Mayuko, Numata Munenori, Mori Tadashi, Inoue Yoshihisa
Department of Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.
Department of Applied Chemistry, Osaka University, 2-1 Yamad-oka, Suita, 565-0871, Japan.
Chemistry. 2017 Aug 22;23(47):11272-11278. doi: 10.1002/chem.201701360. Epub 2017 Jul 11.
Saccharide sensing in aqueous media is an intriguing but challenging goal in current chemistry. Herein we report the oligosaccharide-sensing behavior of newly synthesized porphyrin-curdlan conjugates, which are random coils in DMSO but become globules in aqueous solutions to induce circular dichroism (ICD) in the biologically accessible spectral region due to the conformational fixation of porphyrin reporters. The magnitude of ICD was significantly varied specifically in the presence of acarbose, a drug for type-2 diabetes, enabling us to detect the aminosaccharide at concentrations down to 200 μm. This result demonstrates that the prêt-á-porter approach, using less-defined reporter-curdlan conjugates, is more advantageous than the traditional haute-couture approach with highly sophisticated hosts in particular in oligosaccharide sensing.
在水介质中进行糖类传感是当前化学领域一个引人关注但具有挑战性的目标。在此，我们报道了新合成的卟啉- 凝胶多糖缀合物的寡糖传感行为，这些缀合物在二甲基亚砜中为无规卷曲，但在水溶液中会形成球状，由于卟啉报告基团的构象固定，在生物可及光谱区域诱导圆二色性（ICD）。在2型糖尿病药物阿卡波糖存在下，ICD的大小有显著特异性变化，使我们能够检测低至200 μM浓度的氨基糖。这一结果表明，使用定义不太明确的报告基团-凝胶多糖缀合物的“现成可用”方法比采用高度复杂主体的传统“高级定制”方法更具优势，尤其是在寡糖传感方面。
