Chiroptical and Lectin Recognition Properties of Glycoconjugated Poly(phenylacetylene)s Featuring Variable Saccharide Functionalities
Chiroptical and Lectin Recognition Properties of Glycoconjugated Poly(phenylacetylene)s Featuring Variable Saccharide Functionalities
复制标题
DOI：
10.1021/ma7020776
复制
发表时间：
2007-11
期刊：
影响因子：
5.5
通讯作者：
I. Otsuka;Takayoshi Hongo;Hiroshi Nakade;A. Narumi;R. Sakai;T. Satoh;H. Kaga;T. Kakuchi
中科院分区：
文献类型：
--
作者：
I. Otsuka;Takayoshi Hongo;Hiroshi Nakade;A. Narumi;R. Sakai;T. Satoh;H. Kaga;T. Kakuchi
本文报道了聚苯乙炔的手性光学性质和凝集素亲和性，这些聚苯乙炔具有糖功能，包括d-吡喃葡萄糖苷和d-吡喃半乳糖苷。以4-乙炔基苯基2，3，4，6-四-O-乙酰基-α-D-吡喃葡萄糖苷（PA-α-Glc-OAc）、β-D-吡喃葡萄糖苷（PA-β-Glc-OAc）、α-D-吡喃半乳糖苷（PA-α-Gal-OAc）和β-D-吡喃半乳糖苷（PA-β-Gal-OAc）为原料，通过铑催化聚合反应合成了糖共轭聚苯乙炔。CD和UV-维斯实验的基础上，这些聚合物被发现有偏见的螺旋构象在各种溶剂中，如CHCl 3，THF和HFIP。使用CH 3 ONa对乙酰基进行脱保护提供了具有不同糖官能度的线性糖阵列;聚-PA-α-Glc、聚-PA-β-Glc、聚-PA-α-Gal和聚-PA-β-Gal。CD实验表明，poly-PA-α-Glc和poly-PA-β-Glc具有相同的螺旋结构，而poly-PA-α-Gal和poly-PA-β-Gal具有不同的螺旋结构。
We report the chiroptical properties and lectin affinities of poly(phenylacetylene)s featuring saccharide functionalities including d-glucopyranoside and d-galactopyranoside. The glycoconjugated poly(phenylacetylene)s were synthesized by rhodium mediated polymerization from phenylacetylene monomers containing a series of saccharide groups; 4-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside (PA-α-Glc-OAc), β-d-glucopyranoside (PA-β-Glc-OAc), α-d-galactopyranoside (PA-α-Gal-OAc), and β-d-galactopyranoside (PA-β-Gal-OAc). On the basis of CD and UV−vis experiments, these polymers were found to have biased helical conformations in a variety of solvents, such as CHCl3, THF, and HFIP. The deprotection of the acetyl groups using CH3ONa provided the linear saccharide arrays with diverse saccharide functionalities; poly-PA-α-Glc, poly-PA-β-Glc, poly-PA-α-Gal, and poly-PA-β-Gal. CD experiments revealed that poly-PA-α-Glc and poly-PA-β-Glc have identical helical structures, and poly-PA-α-Gal and poly-PA-β-Gal...