108794-37-2Relevant articles and documents
Design and synthesis of 2'-deoxy-2'-fluorodisaccharides as mechanism- based glycosidase inhibitors that exploit aglycon specificity
McCarter, John D.,Yeung, Wai,Chow, Jack,Dolphin, David,Withers, Stephen G.
, p. 5792 - 5797 (2007/10/03)
Stable, aglycon-specific inactivators of glycosidases have considerable potential as tools in the study of mechanisms of oligosaccharide processing, and possibly as avenues toward new therapeutics. Glycosidases for which the rate-determining step with the
2'-FLUOROMALTOSE: SYNTHESIS AND PROPERTIES OF 4-O-(2-DEOXY-2-FLUORO-α-D-GLUCOPYRANOSYL)-D-GLUCOPYRANOSE, AND THE CRYSTAL STRUCTURE OF 2,3-DI-O-ACETYL-1,6-ANHYDRO-4-O-(3,4-TRI-O-ACETYL-2-DEOXY-2-FLUORO-α-D-GLUCOPYRANOSYL)-β-D-GLUCOPYRANOSE
Shelling, Judith G.,Dolphin, David,Wirz, Peter,Cobbledick, Roger E.,Einstein, Frederick W. B.
, p. 241 - 260 (2007/10/02)
Coupling of 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide and 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl bromide with 2,3-di-O-acetyl-1,6-anhydro-β-D-glucose, under Koenigs-Knorr reaction conditions gave, in both instances, only the corresponding α-(1->4)-linked disaccharides.In the first case, the linkage was verified by 1H- and 19F-n. m. r., and by X-ray crystallographic analysis of 2,3-di-O-acetyl-1,6-anhydro-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl)-β-D-glucopyranose.Deprotection of this disaccharide gave 2'-deoxy-2'-fluoromaltose.Maltose and its fluorinated analogue displayed similar 1H- and 13C-n. m. r. spectra and optical rotations, indicating that these two sugars are isomorphous in solution and suggesting that 2'-deoxy-2'-fluoromaltose might be a suitable substrate for studies of α-glycosidases.