Sulfated saccharides

A sulfated saccharide mimetics which inhibit cell adhesion and migration are lead compounds towards a biologically active biodegradable drug. Presented at Eurocarb 14, Liibeck, 2 July 2007. 

To use the proper translation to molar quantities and ratios, we accept that complexing of the steroid molecule will involve a chain of about seven sugar units (as shown by molecular model or the performance of the preformed cyclodextrins). Thus the effective molar saccharide unit has a molecular weight of about 2500 (a seven-membered, sulfated saccharide unit) even though the material used may have anominal molecular weight many times greater (heparin). This, in fact, is consistent with the... 

PoweU, A. K., Ahmed, Y. A., Yates, E. A., Turnbull, J. E. (2010). Generating heparan sulfate saccharide libraries for glycomics apphcations. Nature Protocols, 5(5), 821—833. 

Positive- and negative-ion f.a.b. spectra of sulfated di-, tetra-, and hexa-saccharides from chondroitin sulfate have been reported. The spectra are characterized by multiple molecular-ions containing varying numbers of counter-cations to the sulfate and carboxylate anions, plus fragment ions... 

In contrast to L-iduronic acid residues, most of which are sulfated at C-2, D-glucuronic acid residues in heparin and heparan sulfate are largely or exclusively nonsulfated. This was especially proved by their susceptibility to periodate oxidation,123 and through characterization of D-glucuronic acid-containing di- and tetra-saccharides from deamina-tive104 109 110 138 or heparinase - heparanase cleavage137,145 of heparin. 

The direct 0-alkylation of the anomeric center (Scheme 1, path C) by treatment of furanoses and pyranoses with base and then with simple alkylating agents, for instance an excess of methyl iodide or dimethyl sulfate, has long been known (1,3). Surprisingly, no studies employing this simple method for syntheses of more-complex glycosides and saccharides have been reported prior to our work (1,37,38). 

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