Glycodendrimer syntheses

RG. 66. Commercially available dendrimer scaffolds commonly used for glycodendrimer syntheses, and general synthetic strategies for synthesis of glycodendrimers. 

Chabre YM, Roy R (2(X)8) Recent trends in glycodendrimer syntheses and applications. Curr Top Med Chem 8 1237-1285... 

Figure 1 Structure of the PAMAM-based glycodendrimer synthesized by Okada and coworkers.

SCHEME 45. AB2-sugar scaffold used in glycodendrimer synthesis.319... 

C. Kieburg and T. K. Lindhorst, Glycodendrimer synthesis without using protecting groups, Tetrahedron Lett., 38 (1997) 3885-3888. 

This review is devoted to the description of synthetic strategies for glycodendrimers synthesis. Dendrimers can be classified into three categories carbohydrate-coated, carbohydrate-centered and carbohydrate-based dendrimer. In this paper we will focus on the third one, in which the core unit is originated from a monosaccharide. Compare to classical Pamam, Boltorn cores, carbohydrate units add much more three dimension information, coded in the chirality in almost each carbon. Various coupling chemistry have been developed and are presented here glycosylation, amide bound formation, and click chemistry (thiol-ene reaction, epoxide - thiol reaction). 

This review is devoted to the description of synthetic strategies for glycodendrimers synthesis. Dendrimers can be classified into three... 

Scheme 16.9. Glycodendrimer synthesis using a safety-catch-type linker.

Furthermore, to avoid the anticipated limitation upon the growth of this type of dendrimer, common when saccharides contain protecting groups, Jayaraman and Stoddart focused on synthesis of glycodendrimers wherein the saccharides were totally unprotected during construction.428... 

H. Al-Mughaid and T. Bruce Grindley, Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol, J. Org. Chem., 71 (2006) 1390-1398. 

Y. M. Chabre, C. Contino-Pepin, V. Placide, T. C. Shiao, and R. Roy, Expedi-tive synthesis of glycodendrimer scaffolds based on versatile TRIS and manno-side derivatives, J. Org. Chem., 73 (2008) 5602-5605. 

Y. Li, Y. Cheng, and T. Xu, Design, synthesis and potent pharmaceutical applications of glycodendrimers A mini review, Curr. Drug Discov. Technol., 4 (2007) 246-254. 

S. J. Meunier, Q. Wang, S.-N. Wang, and R. Roy, Synthesis of hyperbranched glycodendrimers incorporating a-thiosialosides based on a gallic acid core, Can. J. Chem., 75 (1997) 1472-1482. 

R. Roy, M.-G. Baek, and K. Rittenhouse-Olson, Synthesis of /V,/V -bis(acryla-mido)acetic acid base-T antigen glycodendrimers and their mouse monoclonal IgG antibody binding properties, J. Am. Chem. Soc., 123 (2001) 1809-1816. 

M.-G. Baek, K. Rittenhouse-Olson, and R. Roy, Synthesis and antibody binding properties of glycodendrimers bearing the tumor related T-antigen, Chem. Commun. (2001) 257-258. 

D. Zanini and R. Roy, Novel dendritic x-sialosides Synthesis of glycodendrimers based on a 3,3 -iminobis(propylamine) core, /. Org. Chem., 61 (1996) 7348-7354. 

Kcnsingcr, R.D., Yowler, B.C., Benesi, A.J., and Schengrund, C.-L. (2004a) Synthesis of novel, multivalent glycodendrimers as ligands for HIV-1 gpl20. Bioconjugate Chem. 15, 349-358. 

Figure 13.10 Synthesis of mannose-/glucose-functionalized dendrimers. For dendrimer loading, x + y = 50% loading was used because optimal activity for glycodendrimers with concanavalin A was previously determined to occur at 50% functionalization. Remaining amines from the poly(amido amine) (PAMAM) substrate were capped as alcohols.

Deguise I, Lagnoux D, Roy R. Synthesis of glycodendrimers containing both fucoside and galactose residues and their binding properties to Pa-IL and PA-IIL lectins from... 

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