In this study, we developed a novel bioeliminable amphiphilic glycopoly(pseudo amino acid), which was synthesized by the condensation polymerization of N-benzyloxycarbonyl-4-hydroxyl-L-proline (NZHpr) followed by the coupling of an alkynyl-functional sugar derivative to the azido-end group, P(NZHpr)(n). The glycosylated P(NZHpr)(n) polymers formed micelles in the aqueous phase. Selective lectin binding experiments confirmed that the glycosylated P(NZHpr)(n) can be used in biorecognition applications. The DOX-loaded micelles facilitated improved uptake of DOX by HeLa cells within 2 h and were primarily retained in the cytoplasm, whereas free DOX tended to accumulate in the nuclei. The DOX-loaded glucosylated P(NZHpr)(n) micelles exhibited a substantially lower cytotoxicity compared to free DOX. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.