Mass spectrometry characterization of 3-OH butyrated β-cyclodextrin

Authors

  • Cristian Peptu,

    1. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania
    2. Institute of Chemistry and Environmental Protection, “Jan Dlugosz'” University of Czestochowa, 13/15 Armii Krajowej Av., 42–200 Czestochowa, Poland
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  • Alina Nicolescu,

    1. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania
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  • Catalina A. Peptu,

    1. Department of Natural and Synthetic Polymers, “Gh. Asachi” Technical University of Iasi, D. Mangeron 71A, 700050 Iasi, Romania
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  • Valeria Harabagiu,

    Corresponding author
    1. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania
    • Petru Poni Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania
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  • Bogdan C. Simionescu,

    1. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania
    2. Department of Natural and Synthetic Polymers, “Gh. Asachi” Technical University of Iasi, D. Mangeron 71A, 700050 Iasi, Romania
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  • Marek Kowalczuk

    1. Institute of Chemistry and Environmental Protection, “Jan Dlugosz'” University of Czestochowa, 13/15 Armii Krajowej Av., 42–200 Czestochowa, Poland
    2. Polish Academy of Sciences, Centre of Polymer and Carbon Materials, 34 M. Sklodowskiej-Curie, 41-819 Zabrze, Poland
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Abstract

Oligo(3-OH butyrate)-β-cyclodextrin esters (PHB-CD) were obtained through ring opening of β-butyrolactone (β-BL) in the presence of β-cyclodextrin (CD) and (-)-sparteine (SP) as nucleophilic activator. The resulted reaction mixture was first separated in two fractions and then investigated through a deep mass spectrometry (MS) study performed on a liquid chromatography-electrospray ionization-quadrupole time of flight (LC-ESI-QTOF) instrument. LC MS and tandem MS structural assignment of the reaction products was completed by NMR. The performed analysis revealed that poly(3-OH butyrate) homopolymers (PHB) are formed together with the PHB-CD products. Secondary reactions resulting in the formation of crotonates were also proved to occur. A comparison between MS and NMR results demonstrated that more than one PHB oligomer is attached to the CD in the PHB-CD product. The tandem MS fragmentation studies validated the proposed structure of CD derivatives. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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