470-16-6

Upstream product

• 124040-55-7 Benzyl-1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructopyranosid 
• 56180-94-0 α-acarbose 
• 57-50-1 Sucrose 
• 921-60-8 L-glucose 
• 41847-61-4 (3S,4S,5R)-2-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetrol 
• 59-92-7 levodopa 
• 124040-50-2 benzyl 1,3,4-tri-O-benzoyl-β-D-fructopyranoside 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 

Downstream Products

• 1462942-88-6 4-[(1'R,2'S,3'R)-3'-(α-D-glucopyranosyloxy)-1',2',4'-trihydroxybutyl]-imidazole 
• 1462942-91-1 4-[(1'R,2'S,3'R)-3'-(α-D-glucopyranosyloxy)-1',2',4'-trihydroxybutyl]-2-methylimidazole 
• 1551576-98-7 2-[(1'R,2'S,3'R)-3'-(α-D-glucopyranosyloxy)-1',2',4'-trihydroxybutyl]quinoxaline 

Relevant academic research and scientific papers

Synthesis of acarbose analogues by transglycosylation reactions of Leuconostoc mesenteroides B-512FMC and B-742CB dextransucrases.

Two new acarbose analogues were synthesized by the reaction of acarbose with sucrose and dextransucrases from Leuconostoc mesenteroides B-512FMC and B-742CB. The major products for each reaction were subjected to yeast fermentation, and then separated and

Enzymatic synthesis of l-DOPA α-glycosides by reaction with sucrose catalyzed by four different glucansucrases from four strains of Leuconostoc mesenteroides

Synthesized by reaction of Leuconostoc mesenteroides B-512FMC, B-742CB, B-1299A dextransucrases, and B-1355C alternansucrase with sucrose and l-DOPA α-glycosides were synthesized by reaction of l-DOPA with sucrose, catalyzed by four different glucansucras

Alternansucrase acceptor reactions with D-tagatose and L-glucose

Alternansucrase (EC 2.4.1.140) is a d-glucansucrase that synthesizes an alternating α-(1→3), (1→6)-linked d-glucan from sucrose. It also synthesizes oligosaccharides via d-glucopyranosyl transfer to various acceptor sugars. Two of the more efficient monosaccharide acceptors are d-tagatose and l-glucose. In the presence of d-tagatose, alternansucrase produced the disaccharide α-d-glucopyranosyl-(1→1)-β-d-tagatopyranose via glucosyl transfer. This disaccharide is analogous to trehalulose. We were unable to isolate a disaccharide product from l-glucose, but the trisaccharide α-d-glucopyranosyl-(1→6)-α-d-glucopyranosyl-(1→4) -l-glucose was isolated and identified. This is analogous to panose, one of the structural units of pullulan, in which the reducing-end d-glucose residue has been replaced by its l-enantiomer. The putative l-glucose disaccharide product, produced by glucoamylase hydrolysis of the trisaccharide, was found to be an acceptor for alternansucrase. The disaccharide, α-d-glucopyranosyl- (1→4)-l-glucose, was a better acceptor than maltose, previously the best known acceptor for alternansucrase. A structure comparison of α-d-glucopyranosyl-(1→4)-l-glucose and maltose was performed through computer modeling to identify common features, which may be important in acceptor affinity by alternansucrase.

NEUE SYNTHESE UND KRISTALLSTRUKTUR DER LEUCROSE

Boron trifluoride-catalyzed condensation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride (2) with 3,4-di-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose (1) gave preferentially the α-D-(1->5)-linked disaccharide 8.Similarly, glycosylation of benzyl 1,3,4-tri-O-benzoyl-β-D-fructopyranoside (4) with 2 gave preponderantly a disaccharide derivative that, after cleavage of benzoyl as well as benzyl groups, afforded leucrose (5-O-α-D-glucopyranosyl-β-D-fructopyranose; 13).This crystallized in the orthorhombic space group P212121 containing four sugar and four water molecules in the unit cell in two positions in the ratio of 4:1.As expected, both the fructopyranose and the glucopyranose rings adopted the 2C5(D) or 4C1(D) chair conformations, respectively.