80312-32-9

Usage

Uses

Used in Pharmaceutical Industry:
4-O-a-D-Glucopyranosylmoranoline is used as an α-glucosidase inhibitor for its potential as an effective oral anti-diabetic agent. It helps in managing blood sugar levels by inhibiting the enzyme α-glucosidase, which is responsible for breaking down complex carbohydrates into simpler sugars that can be absorbed by the body. This action may contribute to better glycemic control in diabetic patients.

InChI:InChI=1/C12H23NO9/c14-5-10(17)8(16)12(19,20)11(18,6-15)22-9(10)21-7-2-1-3-13-4-7/h7-9,13-20H,1-6H2/t7?,8-,9+,10-,11-/m1/s1

Upstream product

• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 108811-21-8 2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucopyranoside 
• 27891-73-2 phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 801287-87-6 methyl 2,2',3,3'-tetra-O-acetyl-4',6'-O-benzylidene-6-deoxy-6-iodo-α,β-D-maltoside 
• 801287-88-7 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α,β-D-xylo-hex-5-enopyranosyde 
• 801287-89-8 methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside 
• 808737-09-9 (2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 

Downstream Products

• 121133-71-9 (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-(4-methyl-benzyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 121133-75-3 4-O-α-D-glucopyranosyl-N-(β-phenylethyl)moranoline 
• 121133-70-8 4-O-α-D-glucopyranosyl-N-(4-bromobenzyl)moranoline 
• 121133-82-2 (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-((E)-3-phenyl-allyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 121133-78-6 (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-(3-phenoxy-propyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 121133-77-5 4-O-α-D-glucopyranosyl-N-(β-phenoxyethyl)moranoline 
• 121133-73-1 (2S,3R,4S,5S,6R)-2-((2R,3R,4R,5S)-1-Benzyl-4,5-dihydroxy-2-hydroxymethyl-piperidin-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 121133-76-4 4-O-α-D-glucopyranosyl-N-(3-phenylpropyl)moranoline 
• 121133-80-0 (2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-(4-phenoxy-butyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Enzymic synthesis of α- and β-D-glucosides of 1-deoxynojirimycin and their glycosidase inhibitory activities

1-Deoxynojirimycin (1) is a potent inhibitor of mammalian and rice α- glucosidase. Several glucosides of 1 were synthesized by use of the native and immobilized enzyme and their effect on various enzymes was investigated. Transglucosylation reactions using rice α-glucosidase, yeast α- and β- glucosidases purified from Rhodotorula lactosa were performed with maltose or cellobiose as a glucose donor and N-(benzyloxycarbonyl)-1-deoxynojirimycin (2) as an acceptor. The transglucosylation reaction using native rice α- glucosidase afforded 3-O-α-D-glucopyranosyl-N-(benzyloxycarbonyl)-1- deoxynojirimycin (4), 4-O-α-D-glucopyranosyl-N-(benzyloxycarbonyl)-1- deoxynojirimycin (5), and 2-O-α-D-glucopyranosyl-N-(benzyloxycarbonyl)-1- deoxynojirimycin (3) in yields of 40, 13, and 2%, respectively, after 30 min. The transglucosylation reaction using immobilized rice α-glucosidase was similar to that using the native enzyme. In the system using native yeast α- glucosidase, 3, 5, and 4 were formed in yields of 34, 13, and 6%, respectively, after 15 h. The immobilization of yeast α-glucosidase caused a significant decrease in transglucosylation activity. Yeast β-glucosidase showed a high transglucosylation activity and incubation with the reaction system afforded 2-O-β-D-glucopyranosyl-N-(benzyloxycarbonyl)-1- deoxynojirimycin (6) and 4-O-β-D-glucopyranosyl-N-(benzyloxycarbonyl)-1- deoxynojirimycin (7) in yields of 69 and 3%, respectively, after 3 h. The transglucosylation reaction using immobilized yeast β-glucosidase preferentially afforded 6 in a yield of 73% after 3 h. After removal of N- benzyloxycarbonyl group from the product glucosides, their glycosidase inhibitory activities were measured. 3-O-α-D-Glucopyranosyl-1- deoxynojirimycin (9) retained the potent inhibition of 1 against rat intestinal sucrase activity and was more effective than 1 against rice α- glucosidase. 4-O-α-D-Glucopyranosyl-1-deoxynojirimycin (10) retained the potency of 1 against rat intestinal sucrase and isomaltase. 2-O-α-D- Glucopyranosyl-1-deoxynojirimycin (8) was more effective than 1 against trehalases. 1-Deoxynojirimycin (1) is a potent inhibitor of mammalian and rice α-glucosidase. Several glucosides of 1 were synthesized by use of the native and immobilized enzyme and their effect on various enzymes was investigated. Transglycosylation reactions using rice α-glucosidase, yeast α and B-glucosidases purified from Rhodotorula lactosa were performed with maltose or cellobiose as a glucose donor and N-(benzyloxycarbonyl)-1-deoxynojirimycin (2) as an acceptor. The immobilization of yeast α-glucosidasse caused a significant decreased in transglucosylation activity.

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

Simple syntheses of 4-O-glucosylated 1-deoxynojirimycins from maltose and cellobiose

Glucosidase inhibitors α-d-glucopyranosyl-(1→4)-1- deoxynojirimycin and β-d-glucopyranosyl-(1→4)-1-deoxynojirimycin were prepared from maltose and cellobiose, respectively, via the corresponding 5,6-eno derivatives, their epoxidation and the subsequent double reductive amination of the resulting 5-uloses. In both cases, the reported route is the first chemical synthesis not based on enzymatic glucosyl transfer.

Enzymatic Preparation of N-Substituted 4-O-&α-D-Glucopyranosylmoranoline Derivatives

A transglycosylation reaction with N-substituted moranolines was carried out with soluble starch as the glucose donor and cyclodextrin glycosyltransferase from Bacillus stearothermophilus, the degree of N-substituted moranolines that were converted to transglycosylation products being within the range of 60 to 81percent.The resultant transglycosylation products were hydrolyzed by glucoamylase from Rhisopus niveus, and the degree of N-substituted moranolines that were converted to N-substituted 4-O-α-D-glucopyranosylmoranolines was within the range of 53 to 72percent.The inhibitory activities of N-substituted 4-O-α-D-glucopyranosylmoranolines against cyclodextrin glycosyltransferase were greater than those of corresponding N-substituted moranolines, and N-substituted 4-O-α-D-glucopyranosylmoranolines lost the inhibitory activities against glucoamylase.Among these N-substituted 4-O-α-D-glucopyranosylmoranolines, the N-methyl derivative was a very potent inhibitor.