Synthesis of the Polymer of 1 {3-O[(R)-1 (L-Alanyl-D-Isoglutamyl Carbonyl) Ethyl]-α-D-Glucopyranos-6-O-Carbonycarbonyl}Ethylene

Abstract

Abstract The polymer of 1- 3-O [(R)1-(L-alanyl-D-isoglutamyl carbonyl)ethyl] α-D-glucopyranos-6-O-carbonyl ethylene was synthesized as a acryloyl type polymer by fixing the D-glucose analog (GADP) of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP), which is the minimum required structure responsible for the immunoadjuvant activity of bacterial cell-wall peptidoglycan. N- [2-(1,2-O-Isopropylidene-6-O-acryloyl-α-D-glucofuranos-3-Oyl)-(R)-propionyl] -L-alanyl-D-isoglutamine benzyl ester (6) was prepared as a key monomer in the synthesis. The homopolymerization of 6 and the copolymerization of 6 with hydrophobic acryloyl monomers were carried out in benzene at 60°C by using 2,2′-azobisisobutyronitrile as a radical initiator to give homopolymer 7 and copolymer 10, respectively. Removal of isopropylidene and benzyl protecting groups from 7, 10 and 8, 11 was carried out by acid treatment with trifluoroacetic acid/water (6:1 v/v) and by catalytic hydrogenolysis with palladium carbon, respectively, to afford the hom...