Synthesis of Poly=1={3-O-(1=(benzyl-L=alanyl Carboxylate)ethyl]-D-glucos=6-O-carbonyl}-1=methylethylene
- 1 April 1983
- journal article
- research article
- Published by Taylor & Francis in Journal of Macromolecular Science: Part A - Chemistry
- Vol. 19 (6) , 853-865
- https://doi.org/10.1080/00222338308060781
Abstract
Poly-1-{3-O-[1-(benzyl-L-alanyl carboxylate)ethyl]-D-glucos-6-O-carbonyl}-1-methylethylene was synthesized as the lipophilic and polymeric models of N-acetylmuramyl-L-alanyl-D-isoglutamine corresponding to the minimal structure required for the immunoadjuvant activity of bacterial cell wall. N-[2-(1,2-O-isopropylidene-6-O-methacryloyl-.alpha.-D-glucofuranos-3-O-yl)propionyl]-L-alanine benzyl ester was prepared from D-glucose through 8 steps as a key monomer in the synthesis. The polymerization of that monomer was carried out in benzene at 50.degree. C by using 2,2''-azobisisobutyronitrile as a radical initiator to give poly-1-{-1, 2-O-isopropylidene-3-O-[1-(benzyl-L-alanyl carboxylate)ethyl]-.alpha.-D-glucofuranos-6-O-carbonyl}-1-methyl-ethylene. The removal of isopropylidene groups in this polymer was carried out by treatment with trifluoroacetic acid (6:1 vol/vol) to give the intended polymer. Characterizations of the polymers obtained were carried out.Keywords
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