The synthesis of decanoate
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-cyclodextrin esters (
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-CDd) and hexanoate
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-cyclodextrin esters (
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-CDh) wasbiocatalyzed by thermolysin from native
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-cyclodextrin (
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-CD) and vinyl hexanoate or vinyl decanoate used asacyl donors. The products were chemically characterized by infrared, NMR, and mass spectrometry. Both
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-CDdand
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-CDh esters were identified as a mixture of
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-CD preferentially substituted on the C2 position by thecorresponding acyl chain. The degree of substitution varied from 2 to 7 for
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-CDd and from 4 to 8 for
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-CDh.The ability of
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-CD esters to self-organize into nanoparticles was tested using a nanoprecipitation technique invarious solvents. The mean size diameter and polydispersity measured by quasi-elastic light scattering weredramatically affected by the nature of solvent (acetone, ethanol, or tetrahydrofuran) used in the nanoprecipitationtechnique. When directly observed using cryo-transmission electron microscopy,
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-CDh appeared as uniformlydense nanospheres, whereas
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-CDd exhibited a multilamellar onion-like organization. A structural model wasrationalized for the
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-CDd nanoparticles.