Abstract
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...
Published Version
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