134039-12-6Relevant articles and documents
Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications
Lin, Geng-Min,Sun, He G.,Liu, Hung-Wen
, p. 3438 - 3441 (2016)
Uridine 5′-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. 19F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.
NEW SYNTHETIC PATHWAYS TO 5-C-ALKOXYPYRANOSIDES AND TO HEXOS-5-ULOSE DERIVATIVES
Barili, Pier Luigi,Berti, Giancarlo,Catelani, Giorgio,D'Andrea, Felicia
, p. 135 - 142 (2007/10/02)
Several new 5-C-alkoxy-D-galactopyranosides have been obtained by oxidation of 4-deoxy-α-L-threo-hex-4-enopyranosides (easily available from β-D-galactopyranosides) with MCPBA in alcoholic solvents.They have been converted into the so far unreported L-ara
A simple stereospecific route to 5-C-alkoxy-D-galactopyranosides and to L-arabino-hexos-5-uloses
Barili,Berti,Catelani,d'Andrea
, p. 959 - 962 (2007/10/02)
5-C-alkoxy-β-D-galactopyranosides, which are easily convertible into L-arabino-hexos-5-uloses, can be prepared from β-D-galactopyranoside via peroxyacid oxidation in an alcoholic solvent of intermediate 4-deoxy-α-L-threo-hex-4-enopyranosides.
