Oligosaccharides analogues

Sujino K, Uchiyama T, Hindsgaul O, Seto NOL, Wakarchuk WW, Palcic MM. Enzymatic synthesis of oligosaccharide analogues UDP-Gal analogues as donors for three retaining a-galactosyltransferases. J. Am. Chem. Soc. 2000 122 1261-1269. 92. 

Compounds with Alkynyl Aglycons. A set of oligosaccharide analogues containing two sugar units and four alkyne bonds have been made as illustrated in Scheme 12. ... 

Fig. 8. Different products with sucrose analogues as substrates.115 Enzymatic synthesis of 1-kestose, 1-nystose, and their analogues by /(-fructofuranosidase of A. niger. Structures of fructo-oligosaccharides (A) commercial products, (B) mannose- (C) galactose-, and (D) xylose-substituted analogues.

Fig. 40. Simple lactoside analogues as surrogates for the more complex GML oligosaccharide ligand against the pentameric bacterial toxin from Vibrio cholerae 09...

A different strategy for the development of carbohydrate mimics has focused on the replacement of the non-pharmacophoric parts of active oligosaccharides by conformationally stable cyclic diols. Thus, looking for an analogue of the a-o-Man/)-(l — 2)-a-D-Man/>-(l — 6)-a-D-Man/)-mannotrioside, one of the terminal arms of the MangGlcNAc2... 

Our strategy for synthesis of the oligosaccharide chains,27.28 calls for 2,6-dideoxyhexoses or the corresponding glycals to serve as precursors for both a- and p-glycosidation reactions. It a selective p-glycosidation protocol can be developed, then in principle any structural isomer or analogue of the natural product can be assembled from a common set of monosaccharide precursors.29... 

RJ Linhardt, T Toida. Heparin Oligosaccharides New Analogues Development and Applications. In ZJ Witczak, KA Nieforth. Carbohydrate as Drugs. New York Marcel Dekker, 1997, pp 277-341. 

A. Oseltamivir inhibits neuraminidase, an enzyme that cleaves neuraminic acid from oligosaccharides. Neuraminidase activity aids the movement of viral particles through neuraminic acid-rich respiratory secretions and is required for the release of progeny virions. Inhibition of viral DNA polymerase is the mechanism of action of nucleoside analogue antiviral drugs. Interferons do stimulate the JAK-STAT signaling pathway but do not stimulate proliferation of immune cells. Ribavirin inhibits GTP synthesis, and the antiretroviral protease inhibitors (e.g., ritonavir) inhibit HIV protease. 

The sulfated oligosaccharides discussed above were highly, but not completely, sulfated so that mixtures of compounds with a slightly different sulfation pattern resulted. An attempt to understand which sulfation site was important for the biological activity of tetrasaccharide 15 was made by the synthesis of mono-and oligodeoxygenated analogues of 15. These tetrasaccharides were prepared in a block synAesis approach comparable to Ae synthesis of 15, and the deoxy Anctions were essentially mtroduced on the di- or tetrasaccharide level. A representative synAetic example is depicted in Scheme 4 [44]. 

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