Abstract
Pure sucrose is inexpensive and readily available, making this disaccharide a highly desirable starting material for new polymers. In order to achieve a clean polymerization, the disaccharide must be regioselectively monofunctionalized in good yield. This paper describes the practical, enzyme-mediated synthesis of sucrose-1 ′-methacrylate 2 from sucrose and vinyl methacrylate using subtilisin Carlsberg (Sigma, Protease VIII), a readily available bacterial serine protease. A key aspect of this process, ascertaining the positional selectivity of acylation, was unambiguously accomplished using 1H-detected (1H, 13C) one-bond shift correlation (HMQC) spectroscopy and1H-detected (1H, 13C) multiple bond correlation (HMBC) spectroscopy.
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