Dialdosides-(1,5) of glucose and galactose: synthesis, reactivity, and conformation

Modification of Galactose Oxidase to Introduce Glucose 6-Oxidase Activity

“…Trace byproducts are believed to be the dimer and a ± b elimination product of the sugar aldehyde. [9,10] The appearance of byproducts after product purification indicates that these substances are generated nonenzymatically. Byproducts with the same retention times were observed in the reaction of native GOase (Sigma) with methyl-b-D-galactopyranoside (data not shown).…”

Cyanodeoxy‐Glycosyl Derivatives as Substrates for Enzymatic Reactions

“…As for compounds carrying a cyano group at the C‐5 position, several methods have been described that yield, for example, methyl α‐ D ‐galactopyranuronitrile ( 4 ) or methyl α‐ D ‐glucopyranuronitrile ( 5 ) (Figure 1). 13–15 2,3,6‐Trideoxy‐6‐cyano derivative 6 and the unsaturated 6‐deoxy‐6‐cyano derivative 7 were prepared by displacement of the corresponding 6‐ O ‐triflate with tetrabutylammonium cyanide 16…”

Stereoselective synthesis of chirally deuterated (S)-d-(6-2H1)glucose

“…Compound 3 was oxidized to methyl 6-aldehydo-2,3,4-tri-O-benzyla-D D -(6-2 H 1 )glucopyranoside 5 in 95% yield under the standard Swern conditions. 18 The 2 H NMR spectrum of 5 showed a signal at d 9.48 ppm indicative of an aldehydic deuterium.…”

“…Alpine-Borane â is a trade name of Aldrich Chemical Co. Normal-phase column chromatography was performed on Silica Gel 60 (230-400 mesh, EM Science). Reversed-phase column chromatography was performed on Bakerbonde C 18 Compound 6 was synthesized as described by FalconeHindley and Davis 11 with some modifications. To a solution of aldehyde 5 (470 mg, 1.02 mmol) in CH 2 Cl 2 at room temperature was added a 0.5 M solution of R-(+)-Alpine-Borane â in THF (6 mL, 3 mmol).…”