ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Poly{1-{3-[O-1-(1-carboxyethylaminocarbonyl)ethyl]-6-O-D-glucopyranosylcarbonyl}ethylene} (3b) was synthesized as the lipophilic and polymeric model of 1-{N-[2-(2-acetylamino-2-deoxy-3-O-D-glucopyranosyl)propionyl]-L-alanylamino}glutamic acid (1) to the minimum required structure for the eimmunoadjuvant activity of bacterial cell wall. N-[2-(6-O-acryloyl-1,2-O-isopropylidene-α-D-3-O-glucofuranosyl)propionyl]-L-alanine benzyl ester (6) was prepared as a key monomer in the synthesis. The homopolymerization of this monomer was carried out in benzene at 50°C using 2, 2′-azoisobutyronitrile as radical initiator to give polymer 7. From the results of copolymerization with styrene, the values of Q and e for the acryloyl type monomer 6 were estimated to be 2,0 and 0,11, respectively. The removal of isopropylidene and benzyl protecting groups from homopolymer 7 was carried out by acidic treatment with trifluoroacetic acid/water (vol. ratio 6:1) and by catalytic hydrogenolysis with palladium carbon in acetone, respectively, to afford the homopolymer 3b.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1984.021850204
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