Helical stereoregular artificial glycoconjugate polymers based on poly(phenylacetylene) backbone: Synthesis and molecular recognition with lectin

摘要

Stereoregular poly(phenylacetylene)s bearing pendant lactose and cellobiose moiety were synthesized by polymerization of beta-N-glycosylated 4-ethynylbenzamides with [Rh(nbd)Ci](2) (nbd=norbornadiene) as initiator. The glycoconjugate polymer possessed alternating double bond backbone with cis-transoidal regioregularity and helical conformation. Inhibition assay of hemagglutination revealed that galactose-specific lectin efficiently bound to the stereoregular helical glycopolymer bearing lactose, but the binding was not so strong as that of the corresponding flexible glycoconjugate polystyrene. [References: 17]