Methyl α d glucopyranoside

Manufactured by Merck Group

Sourced in United States

Methyl-α-d-glucopyranoside is a carbohydrate derivative used in laboratory settings. It is a synthetic compound consisting of a glucose molecule with a methyl group attached. The compound is commonly utilized as a reference standard or reagent in various analytical and research applications.

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7 protocols using methyl α d glucopyranoside

Isolation of Native Proteins from H. contortus

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Native proteins were isolated from adult H. contortus by Con A lectin-agarose (Vector laboratories, Newark, CA, USA) as reported previously [22 (link)]. In brief, 800 adult worms were homogenized in a tris-buffered saline buffer containing 1.0% v/v Triton X-100 for 30 min in a glass homogenizer. The homogenate was centrifuged at 2500 g for 20 min. The supernatant was filtered (0.22 μm) and purified by Con A lectin-agarose. The bound samples were extensively rinsed with a 0.25% v/v Triton X-100 buffer, followed by the elution of proteins in a buffer containing 200 mM methyl-α-D-mannopyranoside (Sigma-Aldrich, St. Louis, MO, USA) and 200 mM methyl-α-D-glucopyranoside (Sigma-Aldrich, St. Louis, MO, USA). The protein concentration was detected using a BCA kit (Beyotime, Shanghai, China).

Ye L., Zhang Y., Wu S., Wang Z., Liu F., Wang C, & Hu M. (2022). Immunoprotection Efficacy of Con A-Purified Proteins against Haemonchus contortus in Goats. Vaccines, 10(11), 1891.

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Quantifying Infectious Virus in Respiratory Samples

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Samples of upper eyelid and trachea were homogenised in the 500 μl volume of PBS they were stored in and serially diluted in TOC infection media (1 X EMEM containing 7.5% methyl α D-glucopyranoside, 1% L-Glutamine, 5% Hepes, 0.5% Nystatin and 0.1% Penicillin/Streptomycin, all obtained from Sigma). The quantity of infectious virus was determined via titration in ex vivo TOCs as previously described [59 ]. Viral titres were calculated using the Reed-Muench method for end point titre calculations [66 ] and presented as CD₅₀/ml.

Keep S., Stevenson-Leggett P., Webb I., Fones A., Kirk J., Britton P, & Bickerton E. (2024). The spike protein of the apathogenic Beaudette strain of avian coronavirus can elicit a protective immune response against a virulent M41 challenge. PLOS ONE, 19(1), e0297516.

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Synthesis of Carbohydrate Derivatives

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Methyl α-d-glucopyranoside (≥99%), tetrabromomethane (99%), triphenylphosphine (99%), anhydrous pyridine (99.8%), sodium dicyanamide (96%), trimethylamine 31–35 wt.% in ethanol solution, and Ludox^® HS-40 colloidal silica (40 wt.% suspension in H₂O) were commercial materials purchased from Sigma-Aldrich. Potassium tricyanomethanide (98%) and potassium tetracyanoborate (97%) were acquired from Strem, Newburyport, MA, USA and SelectLab Chemicals, Münster, Germany respectively. Silver nitrate (99.9%) was received from POCH, Gliwice, Poland. N-(6-Deoxy-1-O-methoxy-α-d-glucopyranoside)-N,N,N-trimethylammonium bromide was synthesized according to a previously described procedure [5 (link)].

Brzęczek-Szafran A., Gaida B., Blacha-Grzechnik A., Matuszek K, & Chrobok A. (2021). Bioderived Ionic Liquids and Salts with Various Cyano Anions as Precursors for Doped Carbon Materials. International Journal of Molecular Sciences, 22(19), 10426.

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Immunoblotting Reagents and Materials

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Reagents were purchased from the following sources: middle range molecular weight protein markers, anti-mouse IgG horseradish peroxidase conjugate, 5-bromo-4-chloro-3 indolyl phosphate (BCIP), nitro blue tetrazolium (NBT), Promega; anti-rabbit IgG alkaline phosphatase conjugate, anti-bovine IgG horseradish peroxidase conjugate, anti-bovine IgG alkaline phosphatase conjugate, anti-equine IgG alkaline phosphatase conjugate, anti-mouse IgG alkaline phosphatase conjugate, diaminobenzidine (DAB), horseradish peroxidase type VI-A, fibrous DEAE-cellulose, benzamidine, iodoacetamide, phenyl methyl sulfonyl fluoride (PMSF), N-N′-1,2 phenylenedimaleimide (o-PDM), N-N′-1,4 phenyllenedimaleimide (p-PDM), gel filtration molecular weight protein marker kit, Staphylococcus aureus V8 protease, concanavalin A (Con A), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), methyl-α-d-mannopyranoside, methyl-α-d-glucopyranoside, Sigma; Q-Sepharose, S-Sepharose, Sefacryl S-300, Pharmacia; pre-stained high molecular weight protein markers, Gibco BRL; sulfosuccinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (sulfo-SMCC), nitrocellulose (0.45 μm pore size), Pierce; broad range isoelectric focusing calibration kit (3–10), Immobilin dry strips (pH 5–8), ampholites (pH 3–10), BioRad. All other chemicals were of the highest quality grade available.

Camargo R., Izquier A., Uzcanga G.L., Perrone T., Acosta-Serrano A., Carrasquel L., Arias L.P., Escalona J.L., Cardozo V, & Bubis J. (2015). Variant surface glycoproteins from Venezuelan trypanosome isolates are recognized by sera from animals infected with either Trypanosoma evansi or Trypanosoma vivax. Veterinary Parasitology, 207(1-2), 17-33.

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Antioxidant Capacity Evaluation Protocol

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2,2-Diphenyl-1-picryl-hydrazyl (DPPH), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), di-potassium peroxodisulphate, 2,4,6-tripyridyl-s-triazine (TPTZ), iron (II) sulphate heptahydrate, iron (III) chloride hexahydrate, ferrozine, iron (II) chloride tetrahydrate, caffeic, p-coumaric and ferulic acids, methyl-α-d-glucopyranoside, phenyl-β-d-glucopyranoside and 1-methylimidazole were purchased from Sigma–Aldrich (USA), while 2,2ʹ-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) acid diammonium salt (ABTS) was obtained from Fluka (USA), and bistrimethylsilylacetamide and trimethylsilylchlorosilane from Regis Technologies (USA). Lignan standards were purchased from PhytoLab (Germany), and linustatin and neolinustatin from Chromadex (Santa Ana, CA, USA).

Waszkowiak K., Gliszczyńska-Świgło A., Barthet V, & Skręty J. (2015). Effect of Extraction Method on the Phenolic and Cyanogenic Glucoside Profile of Flaxseed Extracts and their Antioxidant Capacity. Journal of the American Oil Chemists' Society, 92(11-12), 1609-1619.

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Cloning and Characterization of YcjR

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The restriction endonucleases, pfu turbo DNA polymerase, and T4 DNA ligase used in the cloning of the gene for YcjR were purchased from New England Biolabs. The PCR cleanup and gel extraction kits were bought from Qiagen. The plasmid miniprep kit, buffers, phenylmethylsulfonyl fluoride (PMSF), DNase I, methyl-α-D-glucopyranoside and Chelex resin were obtained from Sigma-Aldrich. Isopropyl-β-D-thiogalactopyranoside (IPTG) and reduced nicotinamide adenine dinucleotide (NADH) were purchased from Research Products International Corporation. Selenomethione (SeMet) was obtained from TCI America. α-Methyl-3-keto-D-glucoside was synthesized as reported previously (9 (link), 15 ).

Mabanglo M.F., Huddleston J.P., Mukherjee K., Taylor Z.W, & Raushel F.M. (2020). Structure and Reaction Mechanism of YcjR, an Epimerase that Facilitates the Interconversion of D-Gulosides to D-Glucosides in Escherichia coli. Biochemistry, 59(22), 2069-2077.

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Enzymatic Synthesis of Valuable Compounds

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Sucrose, lactose monohydrate, n-decosan, butanone, methyl tert-butyl ether (Across Organics), Orafti inulin (DP = 2-9, BENEO GmbH, Mannheim, Germany), acetone, ethyl acetate, anhydrous sodium carbonate and sulfuric acid 96% (Chimopar, Bucures , ti, Romania) were used as-purchased from the vendors. Candida antarctica B (Novozyme 435) and Thermomyces lanuginosus lipases were purchased from Novozymes A/S (Bagsvaerd, Denmark). 3-(4-Hydroxyphenyl) propionic acid (HPPA, 97%), tert-butanol (≥99%), molecular sieves (4A, 4-8 mesh), methyl-α-d-glucopyranoside, octyl-β-d-glucopyranoside, N,N-dimethylformamide, α-d-glucose, 1-octanol, 3-(4-hydroxyphenyl) propionic acid methyl ester (HPPME), ferulic acid, caffeic acid, p-coumaric, gallic acid, vanillic acid, ethyl ferrulate, propyl gallate, protocatechuic acid ethyl ester, Pseudomonas fluorescence lipase were from Sigma-Aldrich. Candida rugosa, A. niger, Rhizopus oryzae, pig pancreas and wheat germ lipases and dimethylsulfoxide (DMSO) were from Fluka. Acetonitrile (99.5%), hexane, tert-amyl alcohol, methanol, sodium hydroxide, chloroform, cyclohexane, 2,2-dimethoxypropane, and toluene-p-sulphonic acid monohydrate 99% were analytical reagents bought from Merck.

Croitoru R., Frissen A.E., Broek L.v.d., Todea A., Motoc M., & Boeriu C.G. (2020). Chemoenzymatic Synthesis of New Aromatic Esters of Mono- and Oligosaccharides. Processes, 8(12), 1638-1638.

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