Abstract
Cyclodextrins (CDs) can be used in various drugs as an auxiliary additive such as a carrier, diluent, and solubilizer for tablet ingredients.1–3 The syntheses of natural oligosaccharide-branched CDs, which showed potential binding to lectin, have been studied for the development of a drug carrier for targeting drug delivery systems. We have already reported the chemo-enzymatic syntheses of three natural oligosaccharide-branched CDs by the transglycosylation of Fmoc-Asn(GlcNAc)-NH-ß-CD (4) with glycosyl asparagines prepared from ovalbumin 4 and human transferrin5 using endo-α-N-acetylglucosaminidase of Mucor hiemalis (Endo-M).6 A large-scale synthesis of these CDs was required for the evaluation of these CDs. However, it is difficult to synthesize a large quantity of these CDs by this method, because of the availability limitations of Endo-M. In this paper, the large-scale chemical synthesis of high-mannose type oligosaccharide-branched CD (3) using glycosylasparagine, H-Asn(GlcNAc2Man6)-OH (1)5 as the starting material, which was used as a transglycosylation substance of Endo-M, was described.
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References
Szejtli, J.: Cyclodextrin Technology, Kluwer Academic Publishers, Netherlands.
Froming, K. H., Szejtli, J.: Cyclodextrin in Pharmacy, Kluwer Academic Publishers, Netherlands.
Uekama, K., Hirayama, F., Irie, T. (1991) Modification of Drug Releases by Cyclodextrin Derivatives, in Duchene, D. (ed.), New Trends in Cyclodextrins and Derivatives, Editions de Sante, Paris, pp. 409–446.
Kadowaki, S., Yamamoto, K., Fujisaki, M., Izumi, K., Tochikura, T. (1990) Purification and characterization of a novel fungal endo-ß-N-acetylglucosaminidase acting on complex oligosaccharides of glycoproteins, Agric. Biol. Chem., 54, 97–106.
Tai, T., Yamashita, K., Ogata-Arakawa, M., Koide, N., Muramatsu, T., Iwashita, S., Inoue, Y., Kobata, A. (1975) Structural studies of two ovalbumin glycopeptides in relation to the endo-ß-N-acetylglucosaminidase specificity, J. Biol. Chem., 250, 8569–8575.
Matsuda, K., Inazu, T., Haneda, K., Mizuno, M., Yamanoi, T., Hattori, K., Yamamoto, K., Kumagai, H. (1997) The chemo-enzymatic synthesis and evaluation of oligosaccharide-branched cyclodextrins, Bio. Med. Chem. Lett., 7, 2353–2356.
T., Hattori, K., Imata, H., Kubota, K., Matsuda, K., Aoyagi, M., Yamamoto, K., **doh, C., Yamanoi, T., Inazu, T. (1996) The synthesis of oligosaccharidebranched cyclodextrins and their interaction with concanavalin A, in Szejtli, J., Szente, L., (ed.), Proceeding of 8th International Cyclodextrins Symposium, Kluwer Academic Publishers, Netherlands, pp. 121–124.
Imata, H., Kubota, K., Hattori, K., Aoyagi, M., **doh, C. (1997) The interaction of oligosaccharide-branched cyclodextrins with immobilized concanavalin A, Polym. J., 29, 563–567.
Imata, H., Kubota, K., Hattori, K., Aoyagi, M., **doh, C. (1997) The specificity of association between concanavalin A and oligosaccharide-branched cyclodextrins with an optical biosensor, Bio. Med. Chem. Lett., 7, 109–112.
Sinister, S. C., Swanson, R. V., Alex, L. A., Bourret, R. B., Simon, M. I. (1993) Assembly and function of a quaternary signal transduction complex monitored by surface plasmon resonance, Nature, 365, 343–347.
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© 1999 Springer Science+Business Media Dordrecht
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Inazu, T. et al. (1999). The Synthesis of Oligosaccharide-Branched Cyclodextrins. In: Labandeira, J.J.T., Vila-Jato, J.L. (eds) Proceedings of the Ninth International Symposium on Cyclodextrins. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4681-4_27
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DOI: https://doi.org/10.1007/978-94-011-4681-4_27
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