Design and synthesis of a new series of amphiphilic peptide-β-cyclodextrins as phase transfer carriers for glucosamine

A new series of amphiphilic beta-cyclodextrins were designed and synthesized by grafting peptide chains on to all primary hydroxyl groups via ester bond formation. The desired amphiphilic structures have been produced from ester connection between the C-6 of beta-cyclodextrin and the carboxyl group of N-acetylated resides: H2N-Leu-COOH, H2N-Leu-Gly-COOH, H2N-Leu-Gly-Leu-COOH, and H2N-Leu-Gly-Leu-Gly-COOH (3a-d). The synthetic pathway involves selective bromination of all primary hydroxyls of beta-cyclodextrins and then substitution with the carboxylate moiety of the mentioned N-acetyl residues in the presence of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene). The ability of the synthetic compounds for extraction and phase transfer of glucosamine, as a hydrophilic organic compound, was then studied. The results showed a considerable ability of these amphiphilic compounds for extraction and a selective tendency of 3c for phase transfer of glucosamine. (C) 2010 Elsevier Ltd. All rights reserved.