Synthesis of an oligosaccharide–polylysine dendrimer with reducing sugar terminals leading to acquired immunodeficiency syndrome vaccine preparation

Abstract

AbstractA novel cellobiose–polylysine dendrimer with reducing sugar terminals was synthesized in which the reactive reducing end of a disaccharide cellobiose was directing outward. Hexa‐O‐benzyl‐4′‐(1‐carboxyethyl)‐cellobioside (HBCEC) was synthesized through the reaction of a 4′‐hydroxyl group of benzyl hexa‐O‐benzyl‐cellobioside with methyl 2‐chloropropionate, followed by the removal of the methyl ester group. HBCEC was reacted with polylysine dendrimer generation 3 (G3) to produce benzylated cellobiose–polylysine dendrimer G3. After debenzylation, a cellobiose–polylysine dendrimer G3 was obtained in which the reducing end of the cellobiose was the terminal group of the dendrimer. For the preparation of a dendrimer‐type acquired immunodeficiency syndrome vaccine, the cellobiose–polylysine dendrimer was reacted with a tripeptide (glycyl–prolyl–leucine) and a cyclic oligopeptide from the human immunodeficiency virus by reductive amination; this produced a tripeptide‐bound cellobiose–polylysine dendrimer and an insoluble compound, respectively. The structure analysis was carried out with NMR and matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 2195–2206, 2005