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Keywords:

  • cyclodextrin;
  • liquid chromatography;
  • mass spectrometry;
  • polyester;
  • tandem mass spectrometry

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