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

A 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. (c) 2005 Wiley Periodicals, Inc.