22160-26-5

Usage

Uses

2-O-α-D-Glucosylglycerol is used to prepare glycoglycerolipid analogs active as antitumor-promoters the influence of the anomeric configuration.

Upstream product

• 76222-77-0 2-O-(β-D-glucopyranosyl)-1,3-O-benzylideneglycerol 
• 67-56-1 methanol 
• 120601-64-1 regaloside G 
• 157024-67-4 (β,β'-dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 584-30-5 laminaribiose 
• 10547-04-3 2-O-β-D-glucopyranosyl-D-erythritol 
• 7158-70-5 leucrose 
• 213265-19-1 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-6-benzyloxymethyl-tetrahydro-pyran 
• 56-81-5 glycerol 
• 57-50-1 Sucrose 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 
• 132201-75-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 36722-53-9 (β,β'-bis-benzoyloxy-isopropyl)-(tetra-O-benzoyl-β-D-glucopyranoside) 
• 113134-96-6 (β,β'-dimethoxy-isopropyl)-(tetra-O-methyl-β-D-glucopyranoside) 
• 158110-30-6 (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol 
• 131831-28-2 (2S)-1-O-acetyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 176966-03-3 1-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 176966-04-4 1-O-decanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 

Relevant academic research and scientific papers

Regio- and stereoselective glucosylation of diols by sucrose phosphorylase using sucrose or glucose 1-phosphate as glucosyl donor

Previously it has been shown that glycerol can be regioselectively glucosylated by sucrose phosphorylase from Leuconostoc mesenteroides to form 2-O-α-d-glucopyranosyl-glycerol (Goedl et al., Angew. Chem. Int. Ed. 47 (2008) 10086-10089). A series of compounds related to glycerol were investigated by us to determine the scope of the α-glucosylation reaction of sucrose phosphorylase. Both sucrose and glucose 1-phosphate (G1P) were applied as glucosyl donor. Mono-alcohols were not accepted as substrates but several 1,2-diols were readily glucosylated, proving that the vicinal diol unit is crucial for activity. The smallest substrate that was accepted for glucosylation appeared to be ethylene glycol, which was converted to the monoglucoside for 69%. Using high acceptor and donor concentrations (up to 2.5 M), sucrose or G1P hydrolysis (with H2O being the 'acceptor') can be minimised. In the study cited above, a preference for glucosylation of glycerol on the 2-position has been observed. For 1,2-propanediol however, the regiochemistry appeared to be dependent on the configuration of the substrate. The (R)-enantiomer was preferentialy glucosylated on its 1-position (ratio 2.5:1), whereas the 2-glucoside is the major product for (S)-1,2-propanediol (1:4.1). d.e. ps of 71-83% were observed with a preference for the (S)-enantiomer of the glucosides of 1,2-propanediol and 1,2-butanediol and the (R)-enantiomer of the glucoside of 3-methoxy-1,2-propanediol. This is the first example of stereoselective glucosylation of a non-natural substrate by sucrose phosphorylase. 3-Amino-1,2-propanediol, 3-chloro-1,2-propanediol, 1-thioglycerol and glyceraldehyde were not accepted as substrates. Generally, the glucoside yield is higher when sucrose is used as a donor rather than G1P, due to the fact that the released phosphate is a stronger inhibitor of the enzyme (in case of G1P) than the released fructose (in case of sucrose). Essentially the same results are obtained with sucrose phosphorylase from Bifidobacterium adolescentis.

Small-molecule glucosylation by sucrose phosphorylase: Structure-activity relationships for acceptor substrates revisited

Sucrose phosphorylase catalyzes the O-glucosylation of awide range of acceptor substrates. Acceptors presenting a suitable 1,2-diol moiety are glucosylated exclusively at the secondary hydroxyl. Production of the naturally occurring compatible solute, 2-O-α-D-glucopyranosyl-sn-glycerol, from sucrose and glycerol is a notable industrial realization of the regio-and stereoselective biotransformation promoted by sucrose phosphorylase. The acceptor substrate specificity of sucrose phosphorylase was analyzed on the basis of recent high-resolution crystal structures of the enzyme. Interactions at the acceptor binding site, observed in the crystal (D-fructosyl) and suggested by results of docking experiments (glycerol), are used to rationalize experimentally determined efficiencies and regioselectivities of enzymatic glucosyl transfer.

A high-yielding biocatalytic process for the production of 2-O-(α-D-glucopyranosyl)-sn-glycerol, a natural osmolyte and useful moisturizing ingredient

(Figure Presented) Fit for industry: Stereochemically pure 2-O-(α-D-glucopyranosyl)-sn-glycerol (αGG) was obtained in high yield from an efficient and selective biocatalytic process (see schematic outline). The sucrose phosphorylase catalyzed transfer of a glucosyl group from sucrose to glycerol unites the main advantages of transglycosidases, glycosyltransferases, and glycosynthases for glycoside synthesis and provides access to αGG as an industrial chemical.

METHOD FOR PRODUCING 2-O-GLYCERYL-ALPHA-D-GLUCOPYRANOSIDE

The present invention relates to a method for producing 2-O-glyceryl-α-D-glucopyranoside (αGG; Figure 1) from a glucosyl donor and a glucosyl acceptor comprising the steps: - providing a sucrose phosphorylase (EC 2.4.1.7), incubating said sucrose phosphorylase with a mixture comprising a glucosyl donor and glycerol as glucosyl acceptor and isolating and/or purifying 2-O-glyceryl-α-D-glucopyranoside.

Identification of alpha-D-glucosylglycerol in sake.

alpha-D-Glucosylglycerol (GG) was found for the first time in sake (Japanese rice wine) in an amount of about 0.5%. GG was also found in miso and mirin which had been brewed by using koji. GG was hydrolyzed into glucose and glycerol in an equimolar ratio with maltase (EC 3.2.1.20, alpha-glucosidase from yeast), but not with emulsin (EC 3.2.1.21, beta-glucosidase from almond). The retention times and mass spectra of trimethylsilyl derivatives by a GC-MS analysis of GG in sake were comparable to those of various GG samples synthesized by glycol cleavage. It was proven that GG in sake consisted of three components, viz., 2-O-alpha-D-glucosyl-glycerol (GG-II), (2R)-1-O-alpha-D-glucosylglycerol (R-GG-I) and (2S)-1-O-alpha-D-glucosylglycerol (S-GG-I). The ratio of the three components in GG was 6:66:28 for sake. It is considered that GG was formed by transglucosylation of the glucosyl groups to glycerol by alpha-glucosidase from koji in the sake mash.

Synthesis of glycosyl glycerols and related glycolipids

Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the α-anomer preferentially. The 2-O-(tetra-O-acetyl-β-glycopyranosyl)-sn-glycerols and 2-O-(β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivative of D-mannose were synthesized.

LILIOSIDE A FROM LILIUM LONGIFLORUM: SYNTHESIS AND ABSOLUTE CONFIGURATION

The absolute configuration of lilioside A, previously isolated from Lilium longiflorum, has been established as 2R by the syntheses of lilioside A and its diastereoisomer from laminaribiose and cellobiose, respectively.

REGALOSIDE A AND B, ACYLATED GLYCEROL GLUCOSIDES FROM LILIUM REGALE

Novel acylated glycerol glucosides, regaloside A and B, both bitter to the taste, have been isolated from the fresh bulbs of Lilium regale.Their structures have been shown by the spectral and chemical evidence to be (2S)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, respectively.Key Word Index - Lilium regale; Liliaceae; acylated glycerol glucosides; p-coumaric acid esters; regaloside A; regaloside B; bitter principles; stereochemistry.

New Phenylpropanoid Glycerol Glucosides from the Bulbs of Lilium Species

The fresh bulbs of the genus Lilium have yielded new phenylpropanoid glycerol glucosides, epi-regaloside A (6b), epi-regaloside C (7b) and epi-regaloside F (10b), as mixtures with the corresponding (2S)-regalosides (6a, 7a and 10a), and regaloside G (11).Compounds 6b and 7b have been obtained from Lilium pardarinum, and 6b, 10b and 11 from L. auratum.The spectroscopic data and chemical evidence have allowed us to assign the structures of 6b, 7b, 10b and 11 as (2R)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-caffeoyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-feruloyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-feruloyl-2-O- β-D-glucopyranosylglycerol, respectively.In addition, jatropham and its glucoside have been detected in the fresh bulbs of L. medeoloides.Several previously reported compounds have also been obtained and identified.Keywords - Lilium pardarinum; Lilium auratum; Lilium medeoloides; Liliaceae; phenolic glycerol glucoside; epi-regaloside A; epi-regaloside C; epi-regaloside F; regaloside G; jatropham