Precision Synthesis of Glycopeptide-Type Sugar Balls and Development of Their Molecular Catalyst and Molecular Recognition

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1. Precision Synthesis of Glycopeptide-Type Sugar Balls :An efficient synthetic method via a reaction of primary amine-terminated dendrimer with sugar derivative-substituted α-amino acid N-carboxyanhydride (NCA) was established for glycopeptide-type sugar balls of well-defined structure. A variety of glycopeptide type-sugar balls were synthesized by the reactions of poly(amido amine) dendrimers of up to the eighth generation with glucose, galactose, and N-acetylglucosamine derivative-substituted L-serine NCAs.2. Analysis of Propagation Rate Acceleration in Radial-Growth Polymerization (RGP) :Ring-opening polymerization of NCAs with primary anime-terminated dendrimer as an initiator was kinetically investigated by means of conductivity measurement. On the basis of the effects of solvents, substituents, temperature, and added cyano-terminated dendrimer on the propagation rate constant, it was concluded that the observed acceleration was due to the increased monomer concentration near the dendrimer surface and the enhanced collision probability arising from the radial-growth from the surface as well.3. Evaluation of Glycopeptide-Type Sugar Balls as Biofunctional Materials :Encapsulation of low molecular weight compounds inside glycopeptide-type sugar balls was investigated using sodium 8-anilino-1-naphthalenesulfonate (ANS) as a probe. The number of the encapsulated ANS molecules appreciably increased when poly(amido amine) dendrimer of the eighth generation was allowed to react with N-acetylglucosamine derivative-substituted NCA in dimethyl sulfoxide. Inhibition experiments of lectin-induced hemagglutination proved that the glycopeptide-type sugar balls possessed much higher molecular recognition ability than the corresponding mono- or oligosaccharides.