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Synthesis of a Thiol-β-cyclodextrin, a Potential Agent for Controlling Enzymatic Browning in Fruits and Vegetables

2013; American Chemical Society; Volume: 61; Issue: 47 Linguagem: Inglês

10.1021/jf403063s

1520-5118

Carmen Manta, Gabriela Peralta-Altier, Larissa Gioia, María F. Méndez, Gustavo Seoane, Karen Ovsejevi,

Enzyme Catalysis and Immobilization

A thiol-β-cyclodextrin was synthesized by a simple and environmentally friendly three-step method comprising epoxy activation of β-cyclodextrin, thiosulfate-mediated oxirane opening, and further reduction of the S-alkyl thiosulfate to a thiol group. The final step was optimized by using thiopropyl-agarose, a solid phase reducing agent with many advantages over soluble ones. β-Cyclodextrin thiolation was confirmed by titration with a thiol-reactive reagent, NMR studies, and MALDI-TOF/TOF. Thiolated cyclodextrin had an average value of one thiol group per molecule. Thiol-β-cyclodextrin proved to be an excellent agent for controlling polyphenol oxidase activity. This copper-containing enzyme is responsible for browning in fruits and vegetables. Under the same conditions, thiol-β-cyclodextrin generated a reductive microenvironment that increased the antibrowning effect on Red Delicious apples compared to unmodified β-cyclodextrin.