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Molecules 2018, 23(9), 2259; https://doi.org/10.3390/molecules23092259

Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis

1
Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 84541 Bratislava, Slovakia
2
“Petru Poni” Institute of Macromolecular Chemistry, Grigore Ghica Voda 41A, 700487 Iasi, Romania
3
Institute of Virology, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, Slovakia
*
Authors to whom correspondence should be addressed.
Received: 20 August 2018 / Revised: 1 September 2018 / Accepted: 3 September 2018 / Published: 5 September 2018
(This article belongs to the Special Issue Advances in Biodegradable Polymers)
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Abstract

Cyclodextrins (CDs) were used in the present study for the ring-opening oligomerization (ROO) of l-lactide (LA) in order to synthesize biodegradable products with possible applications in pharmaceutical and medical fields. The practical importance of ROO reactions may reside in the possibility of synthesizing novel CD derivatives with high purity due to the dual role played by CDs, the role of the initiator through the hydroxylic groups, and the role of the catalyst by monomer inclusion in the CD cavity. The analyzed compounds were CDs modified with oligolactides obtained through ROO reactions of l-lactide in dimethylformamide. The resulting CD isomeric mixtures were investigated using classical characterization techniques such as gel permeation chromatography and nuclear magnetic resonance. Moreover, advanced mass spectrometry (MS) techniques were employed for the determination of the average number of monomer units attached to the cyclodextrin and the architecture of the derivatives (if the monomer units were attached as a single chain or as multiple chains). Thus, fragmentation studies effectuated on two different instruments (ESI Q-TOF and MALDI TOF) allowed us to correlate the size of the oligolactide chains attached to the CD with the observed fragmentation patterns. View Full-Text
Keywords: cyclodextrin; oligolactide; mass spectrometry; ring-opening oligomerization; MALDI; ESI; collision-induced dissociation; laser-induced dissociation; biodegradable polymers cyclodextrin; oligolactide; mass spectrometry; ring-opening oligomerization; MALDI; ESI; collision-induced dissociation; laser-induced dissociation; biodegradable polymers
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Peptu, C.; Danchenko, M.; Škultéty, Ľ.; Mosnáček, J. Structural Architectural Features of Cyclodextrin Oligoesters Revealed by Fragmentation Mass Spectrometry Analysis. Molecules 2018, 23, 2259.

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