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

Abstract

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-4Ј-(1-carboxyethyl)-cellobioside (HBCEC) was synthesized through the reaction of a 4Ј-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. 13 (36 mg, 8.7 mol) and Gly-Pro-Leu (20 mg, 70 mol) were dissolved in a 0.1 M borate buffer (pH 9.0, 5 mL). After BH 3 /pyridine (80 mL, 800 mmol) was added, the solution was stirred at 37°C for 5 days. The resulting compound was purified by dialysis and then freeze-dried from water to produce Gly-Pro-Leu-cellobiose-polylysine dendrimer G3 (14; 32 mg) as a white powder. Preparation of Cyclic V3 Loop-Cellobiose-Polylysine Dendrimer G3The cyclic V3 loop (10 mg, 3 mmol) was suspended in 5 mL of a 0.1 M borate buffer (pH 9.0). After cellobiose-polylysine dendrimer (12 mg, 3 mmol) and BH 3 /pyridine (12 mL, 118 mmol) were added, the suspension was stirred at 37°C for 5 days. OLIGOSACCHARIDE-POLYLYSINE DENDRIMER

Chemical surface modification of poly(ethylene terephthalate) fibers by aminolysis and grafting of carbohydrates

“…Immobilization of bioactive molecules on material surfaces represents a major field of research with a wide range of applications 1–7. The grafting of peptides or proteins is well documented,8–10 whereas the grafting of carbohydrates and moreover of complex carbohydrates is less common 11–15.…”

Sulfated oligosaccharide cluster with polylysine core scaffold as a new anti-HIV dendrimer

“…Dendritic compounds of polylysine or carbosilane core scaffolds with sialic acid on their surface were potent inhibitors of influenza viruses, depending on the cluster effects (Roy et al, 1993). An acyclic oligopeptide from HIV connects to cellobiose on the surface of a polylysine dendrimer (Baigude et al, 2005). This type of dendrimer may become an AIDS vaccine.…”

Hyperbranched 5,6-glucan as reducing sugar ball

“…23,[33][34][35][36][37][38][39][40][41][42][43][44][45][46] Spherical macromolecular architectures with their surfaces covered with sugars are of increasing interest due to their unique structures along with specific properties, such as the glycolcluster or multivalent effect on the carbohydrate-protein interactions. For a spherical polymer with many terminal sugar residues, there are a few types of glycodendrimers, e.g., dendrimers prepared from the reaction of the dendrimer surface with mono-and disaccharides (sugar ball), [47][48][49][50][51][52][53][54][55][56][57][58][59] and dendrimers prepared through the convergent method using semi-dendritic branched oligosaccharides. [60][61][62][63][64] Although the synthesis of such glycodendrimer types was accomplished, dendrimers essentially consisting of sugar units, i.e., dendritic carbohydrate polymers, have not been prepared until now due to the complicated and time-consuming synthetic process involving numerous protection, deprotection, and purification procedures.…”