Synthesis of the Polymer of 1 {3-O[(R)-1 (L-Alanyl-D-Isoglutamyl Carbonyl) Ethyl]-α-D-Glucopyranos-6-O-Carbonycarbonyl}Ethylene
作者:
Tatsuro Ouchi,
Toshiyuki Emura,
Takashi Taniguchi,
Itsuo Maeda,
期刊:
Journal of Macromolecular Science: Part A - Chemistry
(Taylor Available online 1988)
卷期:
Volume 25,
issue 12
页码: 1527-1542
ISSN:0022-233X
年代: 1988
DOI:10.1080/10601328808055086
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
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 theD-glucose analog (GADP) ofN-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 homopolymer 9 and the copolymer 12.
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