13121-44-3

Upstream product

• 34339-69-0 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide 
• 1064663-89-3 1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-D-glucitol 

Relevant academic research and scientific papers

Synthesis and comparative structure-activity study of carbohydrate-based phenolic compounds as α-glucosidase inhibitors and antioxidants

Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure-activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro -D-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

ANALYSIS OF LINKAGE POSITIONS IN D-GLUCOPYRANOSYL RESIDUES BY THE REDUCTIVE-CLEAVAGE METHOD

The positions of linkage in the D-glucans amylose, cellulose, laminaran, pullulan were established by permethylation and subsequent reductive cleavage with triethylsilane and either trimethylsilyl trifluoromethanesulfonate (Me3SiO3SCF3) or boron trifluori