Glycomimetics

A. Patel and T. B. Lindhorst, Multivalent glycomimetics Synthesis of nonava-lent mannoside clusters with variation of spacer properties, Carbohydr. Res., 341 (2006) 1657-1668. 

R. Roy, M. Corazon Trono, and D. Giguere, Effects of linker rigidity and orientation of mannoside clusters for multivalent interactions with proteins, in R. Roy, (Ed), Glycomimetics Modern Synthetic Methodologies, ACS Symp. Ser., 896 (2005) 137-150. 

C. Grandjean, G. Angyalosi, E. Loing, E. Adriaenssens, O. Melnyk, V. Pancre, C. Auriault, and H. Gras-Masse, Novel hyperbranched glycomimetics recognized by the human mannose receptor Quinic or shikimic acid derivatives as mannose bioisosteres, ChemBioChem, 2 (2001) 747-757. 

Preparation of polyhydroxylated 6-oxanortropane glycomimetics (e.g. 32), structurally related to the glycosidase inhibitor family of the calystegines, was reported. The synthetic strategy involves the furanose/piperidine... 

Fig. 11 Furanose/piperidine rearrangement in the synthesis of 6-oxanortropane glycomimetics.

Preparation of penta-substituted C8-glycomimetics (e.g. 72) and their glycosidase inhibitory activity was recently studied (Fig. 25).38... 

Different strategies have been developed in order to block the anomeric reactivity of the glycosidic linkage, all based on the substitution of the acetal function with a more stable function. In order to do that, one of the two acetal oxygen atoms, or both, must be replaced. Fig. 1 schematically shows the possible modifications of the anomeric centre generating glycomimetics. 

A. Steiner, A. Stiitz, and T. Wrodnigg, Sulfur-containing glycomimetics, in B. O. Fraser-Reid,... 

S. Hanessian and H. Prabhanjan, Design and synthesis of glycomimetic protolypes-a model sialyl Lewis ligand for E-selectin, Synlett p. 868 (1994). 

Glycomimetics are synthetic carbohydrate analogues whose structure has been simplified and modified after the manner of biomolecules. Such active ingredients are used in the treatment of chronic inflammatory ailments such as rheumatism, dermatitis, and psoriasis. 

SCHEME 10.16 Synthesis of CS glycomimetic polymers through ROMP. 

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