134733-76-9

Upstream product

• 2280-44-6 D-Glucose 
• 60-12-8 2-phenylethanol 
• 76870-86-5 2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 103-82-2 phenylacetic acid 
• 604-69-3 β-D-glucose pentaacetate 
• 492-61-5 β-D-glucose 
• 56401-20-8 α-D-Glucopyranoside 1-(disodium phosphate) 
• 153-18-4 rutin 
• 134698-99-0 phenylethyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3458-28-4 D-Mannose 
• 1259428-61-9 2-phenylethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 

Downstream Products

• 76870-86-5 2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 60-12-8 2-phenylethanol 
• 860648-07-3 phenethyl 6-O-trityl-β-D-glucopyranoside 
• 860648-09-5 phenethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 860648-08-4 phenethyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 860648-10-8 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 
• 129932-48-5 2-phenylethyl β-primeveroside 
• 132278-39-8 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 
• 88510-08-1 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside 
• 88510-13-8 phenylethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside 
• 125572-77-2 2-phenylethyl 1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 
• 911817-13-5 2-phenylethyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 1436383-91-3 2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant academic research and scientific papers

Sensitive and Selective Screening for 6′-O-Malonylated Glucoconjugates in Plants

Using synthesized reference compounds a screening for benzyl, 2-phenylethyl, geranyl, citronellyl, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone 6′-O-malonyl β-D-glucopyranosides in various plant tissues was performed by high-performance liquid chromatography - electrospray ionization - tandem mass spectrometry (HPLC-ESI-MS/MS). The results obtained with fruits (guava; raspberry; strawberry), leaves (green tea; vine), and mountain papaya (Carica pubescens) peel indicate that malonylation of glycoconjugates is a common pathway in plant secondary metabolism.

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

2-: O-Benzyloxycarbonyl protected glycosyl donors: A revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

By reviving an old idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O-2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1,2-trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum

Abstract Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous α-glucosides. In contrast, much less research has been done with respect to the production of β-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENGTM 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various β-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl β-D-glucopyranosides, also the formation of vanillyl 4-O-β-D-glucopyranoside, 2-phenylethyl β-D-glucopyranoside, β-citronellyl β-D-glucopyranoside and 1-O-β-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl β-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl β-D-glucopyranoside.

Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from Cistanche tubulosa

A short synthetic approach was developed for the synthesis of a common trisaccharide core found in kankanose, kankanoside F, H1, H 2, and I isolated from the medicinally active plant Cistanche tubulosa. All glycosylations were carried out under nonmetallic reaction conditions. Yields were very good in all intermediate steps.

Using ionic liquid cosolvents to improve enzymatic synthesis of arylalkyl β-d-glucopyranosides

Enzymatic synthesis of various arylalkyl β-d-glucopyranosides catalyzed by prune (Prunus domestica) seed meal via reverse hydrolysis in the mixture of organic solvent, ionic liquid (IL) and phosphate buffer was described. Among four hydrophilic organic solvents tested, ethylene glycol diacetate (EGDA) was found to be the most suitable for enzymatic synthesis of salidroside, a bioactive compound of commercial interest, from d-glucose and tyrosol. The effects of the nature of ionic liquids and their contents on the enzymatic glucosylation were studied. The addition of a suitable amount of ILs including denaturing ones was favorable to shift the reaction equilibrium toward the synthesis, thus improving the yields. Among the examined ILs, the novel IL [BMIm]I proved to be the best. And this IL was applied as the solvent in biocatalysis for the first time. The yields were found to be enhanced between 0.2-fold and 0.5-fold after the addition of 10% (v/v) [BMIm]I. In 10% (v/v) [BMIm]I-containing system, the desired arylalkyl β-d-glucopyranosides were synthesized with 15-28% yields, among which salidroside was obtained with a yield of 22%. .

Synthesis, biological activity of salidroside and its analogues

Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs-Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl) methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

FimH antagonists for the oral treatment of urinary tract infections: From design and synthesis to in vitro and in vivo evaluation

Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pili, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of α-d-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.

Interactions of aromatic mannosyl disulfide derivatives with Concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies

α-d-Mannopyranosyl units were attached to an aromatic scaffold through disulfide linkages to obtain mono- to trivalent glycosylated ligands for lectin binding studies. Isothermal titration calorimetric (ITC) measurements indicated that binding affinities of these derivatives to Concanavalin A (Con A) were comparable to or slightly higher than that of methyl α-d-mannopyranoside (Ka values in the range of 104 M-1). The stoichiometries of the lectin-ligand complexes were in agreement with the formal valencies (1-3) of the respective ligands indicating cross-linking in interactions with the di- and trivalent derivatives. Multivalency effects could not, however, be observed with the latter. These ligands were shown to bind to the carbohydrate binding site of Con A using saturation transfer difference (STD) NMR competition experiments.