Abstract
The regioselective transesterification of native α- and β-Cyclodextrins (CDs) with vinyl acetate and vinyl laurate is presented in this paper. The reactions were carried out in dimethyl sulfoxide by using low molecular weight salts (Na2HPO4 and NaCl, respectively). MALDI-TOF mass spectrometry and NMR analysis were applied to investigate the chemical structure and the degree of the modification of the final products. Results show that these salts catalyze regioselective transesterification between β-CDs and vinyl laurate aiming for the secondary C-2 hydroxyl group. The synthesis and separation of β-CD-laurate derivatives leads to a mixture of mono-2-O-dodecanoyl-β-CD and native β-CDs. Unreacted β-CDs could be selectively removed enzymatically by cyclodextrin glucosyl-transferase (CGTase) and β-amylase.
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