Sugar acrylate-based polymers as chiral molecularly imprintable hydrogels

✍ Scribed by Xiao-Chuan Liu; Jonathan S. Dordick

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 169 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990601)37:11<1665::aid-pola12>3.0.co;2-3

✦ Synopsis

New polymeric hydrogels with molecular imprinting properties were prepared from enzymically generated sugar acrylates. These so called MIPs (molecularly imprinted polymers) were used as chiral stationary phases for the resolution of the D- and L-isomers of CBz-Asp in polar organic eluants. In the presence of 25% (mol/mol) methyl-␣-D-glucopyranoside-6-acrylate [the balance consisting of N,NЈ-methylenebisacrylamide (BIS)], a separation factor of nearly 2.5 is achieved. The effectiveness of separation was dependent on the nature of the solvent used as eluant and the sugar incorporated into the MIP. Molecular modeling revealed that hydrogen bonding between the sugar and CBz-Asp strongly influences chiral resolution. The broad array of sugars available and their ability to be modified selectively with the use of biocatalysts in both aqueous and organic media may provide a wide range of new imprinted materials for use in separations, sensing, and catalysis.