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Reference type: Journal
Authors: Wulff G, Haarer J
Article Title: Enzyme-analog built polymers .29. The preparation of defined chiral cavities for the racemic-resolution of free sugars.
Publication date: 1991
Journal: Makromolekulare Chemie-Macromolecular Chemistry And Physics
Volume: 192
Issue: (6)
Page numbers: 1329-1338.
DOI: 10.1002/macp.1991.021920610

Abstract: New types of macroporous polymers containing chiral cavities were prepared for the racemic resolution of free sugars. As template monomers 6-O-methyl- and 6-O-benzyl-alpha-D-galactopyranose 1,2;3,4- tetra-O-bis(4-vinylphenylboronate) (3c and b) as well as 1-O-methyl- and 1-O-benzyl-beta-D-fructopyranose 2,3;4,5-tetra-O-bis(4- vinylphenylboronate) (4c and b) were copolymerized with a large amount of ethylene dimethacrylate. After splitting off the respective templates, these polymers were used for the racemic resolution of the racemates of D,L-galactose and D,L-fructose, and also the racemates of 1-O-methyl- and 1-O-benzyl-D,L-fructose. The polymer prepared from 3 b yielded the highest selectivity for the racemic resolution of D,L-galactose. In the case of fructose the benzyl-ether-imprinted polymers yielded the highest selectivity, especially for 1-O-methyl- D,L-fructose separation. Polymers imprinted with D-galactose derivatives showed inverse selectivity by preferably absorbing L- fructose from the racemate. Polymerization at lower temperatures usually yielded more selective polymers


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