Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior Original Research Article

Carboxymethylated cyclosophoraoses (CM-Cys) were synthesized by chemical modification of a family of neutral cyclosophoraoses isolated from Rhizobium leguminosarum biovar trifolii. Structural analyses of the CM-Cys were carried out using NMR and FTIR spectroscopies, and the molecular weight distributions were confirmed with MALDI-TOF mass spectrometry. Based on structural characterization, native cyclosophoraoses were successfully substituted with carboxymethyl groups at the OH-4 and OH-6 of the glucose residues with degrees of substitution (DS) ranging from 0.012 to 0.290. CM-Cys was also used as a host for the inclusion complexation with hydrobenzoin (HB) and N-acetyltryptophan (N-AcTrp) as guest molecules. NMR spectroscopic analyses of the complexes showed that the CM-Cys induced chemical shifts of some protons of the guest molecules upon the complexation. Phase solubility studies of the guest molecules by CM-Cys were performed using HPLC, and the results were compared with those of native cyclosophoraoses. The solubility of HB and N-AcTrp was enhanced by the CM-Cys about 5.1- and 299-fold, respectively.