Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

Abstract

Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 110 °C was investigated considering the structural composition of the products. The obtained products were thoroughly characterized via mass spectrometry methods with soft ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI). Liquid chromatography (LC) separation with evaporative light scattering detection (ELSD) and NMR analysis were employed in order to elucidate the structural profiles of the obtained mixtures. The results clearly demonstrate that the cyclodextrins were tethered with more than one short oligolactate chain per CD molecule, predominantly at the methylene group, through ring opening of L-LA initiated by primary OH groups.

Keywords

• cyclodextrin
• ESI
• evaporative light scattering detection
• liquid chromatography
• L-lactide
• MALDI
• mass spectrometry
• NMR