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Rydz, Joanna, 2022, "Research data for the publication 'Cyclodextrin-oligocaprolactone derivatives – Synthesis and advanced structural characterization by MALDI mass spectrometry'", https://doi.org/10.18150/TI2SFQ, RepOD, V1
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β-Cyclodextrin's involvement in the synthesis and characterization of new β-cyclodextrin-oligocaprolactone (βCDεCL) products obtained via the organo-catalyzed ring-opening of ε-caprolactone has been investigated. The approach consisted of solution polymerization (dimethyl sulfoxide and dimethylformamide) to obtain homogeneous βCDεCL derivatives. Oligomerization kinetics, performed by a MALDI MS optimized method in tandem with 1H NMR, revealed that monomer conversion occurs in two stages: first, the monomer is rapidly attached to the secondary OH groups of β-cyclodextrin and, secondly, the monomer conversion is slower with attachment to the primary OH groups. Further studies of MALDI MS was employed for the measurement of the ring-opening kinetics to establish the influence of the solvents as well as the effect of organocatalysts (4-dimethylaminopyridine and (-)-sparteine). Additionally, the mass spectrometry structural evaluation was further enhanced by fragmentation studies which confirmed the attachment of oligoesters to the cyclodextrin and the cleavage of dimethylformamide amide bonds during the ring-opening process.
Zbadano udział β-cyklodekstryny w syntezie i charakterystyce nowych produktów β-cyklodekstryna-oligokaprolakton (βCDεCL) otrzymanych w wyniku organicznie katalizowanego otwarcia pierścienia ε-kaprolaktonu. W celu otrzymania homogenicznych pochodnych βCDεCL przeprowadzono polimeryzację w roztworze (dimetylosulfotlenku i dimetyloformamidu). Kinetyka oligomeryzacji, przeprowadzona zoptymalizowaną metodą MALDI MS/MS połączoną z 1H NMR, ujawniła, że konwersja monomeru zachodzi w dwóch etapach: po pierwsze, monomer jest szybko przyłączany do drugorzędowych grup OH β-cyklodekstryny, a po drugie, konwersja monomeru jest wolniejsza wraz z przyłączeniem do pierwszorzędowych grup OH. Dalsze badania MALDI MS wykorzystano do pomiaru kinetyki otwarcia pierścienia w celu ustalenia wpływu rozpuszczalników, jak również wpływu organicznych katalizatorów (4-dimetyloaminopirydyny i (-)-sparteiny). Dodatkowo, ocena strukturalna za pomocą spektrometrii masowej została wzbogacona o badania fragmentacyjne, które potwierdziły przyłączenie oligoestrów do cyklodekstryny oraz rozszczepienie wiązań amidowych dimetyloformamidu podczas procesu otwierania pierścienia.
cyclodextrin, ε-caprolactone, cyclodextrin-oligoester, MALDI mass spectrometry, tandem MS, NMR spectroscopy, ring-opening oligomerization, kinetics, biodegradable polyesters, cyklodekstryna, ε-kaprolakton, oligoester-cyklodekstryna, spektrometria masowa MALDI, spektroskopia NMR, oligomeryzacja z otwarciem pierścienia, kinetyka, poliestry biodegradowalne
C. Peptu, D.-A. Blaj, M. Balan-Porcarasu, J. Rydz, Cyclodextrin-oligocaprolactone derivatives – Synthesis and advanced structural characterization by MALDI mass spectrometry, Polymers 14, 1436, 2022, https://doi.org/10.3390/polym14071436 https://doi.org/10.3390/polym14071436 doi: 10.3390/polym14071436
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