3646-73-9Relevant academic research and scientific papers
Structural determination of a neutral exopolysaccharide produced by Lactobacillus delbrueckii ssp. bulgaricus LBB.B332
Sanchez-Medina, Inmaculada,Gerwig, Gerrit J.,Urshev, Zoltan L.,Kamerling, Johannis P.
, p. 2735 - 2744 (2007)
The neutral exopolysaccharide produced by Lactobacillus delbrueckii ssp. bulgaricus LBB.B332 in skimmed milk was found to be composed of d-glucose, d-galactose, and l-rhamnose in a molar ratio of 1:2:2. Linkage analysis and 1D/2D NMR (1H and 13C) studies carried out on the native polysaccharide as well as on an oligosaccharide generated by a periodate oxidation protocol, showed the polysaccharide to consist of linear pentasaccharide repeating units with the following structure:{A figure is presented}.
Exopolysaccharide Produced by Probiotic Bacillus albus DM-15 Isolated From Ayurvedic Fermented Dasamoolarishta: Characterization, Antioxidant, and Anticancer Activities
Kalimuthu, Palanisamy,Ma, Yongkun,Mathivanan, Krishnamurthy,Rai, Amit Kumar,Saravanan, Kandasamy,Sathiyanarayanan, Ganesan,Sekar, Soundarapandian,Sudharsan, Kumaresan,Vinothkanna, Annadurai
, (2022/03/31)
An exopolysaccharide (EPS) was purified from the probiotic bacterium Bacillus albus DM-15, isolated from the Indian Ayurvedic traditional medicine Dasamoolarishta. Gas chromatography-mass spectrophotometry and nuclear magnetic resonance (NMR) analyses revealed the heteropolymeric nature of the purified EPS with monosaccharide units of glucose, galactose, xylose, and rhamnose. Size-exclusion chromatography had shown the molecular weight of the purified EPS as around 240 kDa. X-ray powder diffraction analysis confirmed the non-crystalline amorphous nature of the EPS. Furthermore, the purified EPS showed the maximum flocculation activity (72.80%) with kaolin clay and emulsification activity (67.04%) with xylene. In addition, the EPS exhibits significant antioxidant activities on DPPH (58.17 ± 0.054%), ABTS (70.47 ± 0.854%) and nitric oxide (58.92 ± 0.744%) radicals in a concentration-dependent way. Moreover, the EPS showed promising cytotoxic activity (20 ± 0.97 μg mL–1) against the lung carcinoma cells (A549), and subsequent cellular staining revealed apoptotic necrotic characters in damaged A549 cells. The EPS purified from the probiotic strain B. albus DM-15 can be further studied and exploited as a potential carbohydrate polymer in food, cosmetic, pharmaceutical, and biomedical applications.
Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth
Morikawa, Toshio,Nakanishi, Yusuke,Inoue, Naoki,Manse, Yoshiaki,Matsuura, Hideyuki,Hamasaki, Shinya,Yoshikawa, Masayuki,Muraoka, Osamu,Ninomiya, Kiyofumi
, (2019/11/03)
Seven new acylated iridoid glycosides, picrorhizaosides A–G (1–7), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six known iridoid glycosides (8–13). The structures of these new iridoids, including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Of the isolates, picrorhizaosides D (4, IC50 = 43.4 μM) and E (5, 35.8 μM); picrosides I (8, 60.7 μM), II (9, 22.3 μM), and IV (11, 59.2 μM); and minecoside (13, 57.2 μM), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μM), ketotifen fumarate (76.5 μM), and tranilast (227 μM).
Characterization of properties and transglycosylation abilities of recombinant α-galactosidase from cold-adapted marine bacterium pseudoalteromonas KMM 701 and its C494N and D451A mutants
Bakunina, Irina,Slepchenko, Lubov,Anastyuk, Stanislav,Isakov, Vladimir,Likhatskaya, Galina,Kim, Natalya,Tekutyeva, Liudmila,Son, Oksana,Balabanova, Larissa
, (2018/10/20)
A novel wild-type recombinant cold-active α-D-galactosidase (α-PsGal) from the cold-adapted marine bacterium Pseudoalteromonas sp. KMM 701, and its mutants D451A and C494N, were studied in terms of their structural, physicochemical, and catalytic properties. Homology models of the three-dimensional α-PsGal structure, its active center, and complexes with D-galactose were constructed for identification of functionally important amino acid residues in the active site of the enzyme, using the crystal structure of the α-galactosidase from Lactobacillus acidophilus as a template. The circular dichroism spectra of the wild α-PsGal and mutant C494N were approximately identical. The C494N mutation decreased the efficiency of retaining the affinity of the enzyme to standard p-nitrophenyl-α-galactopiranoside (pNP-α-Gal). Thin-layer chromatography, matrix-assisted laser desorption/ionization mass spectrometry, and nuclear magnetic resonance spectroscopy methods were used to identify transglycosylation products in reaction mixtures. α-PsGal possessed a narrow acceptor specificity. Fructose, xylose, fucose, and glucose were inactive as acceptors in the transglycosylation reaction. α-PsGal synthesized -α(1→6)- and -α(1→4)-linked galactobiosides from melibiose as well as -α(1→6)- and -α(1→3)-linked p-nitrophenyl-digalactosides (Gal2-pNP) from pNP-α-Gal. The D451A mutation in the active center completely inactivated the enzyme. However, the substitution of C494N discontinued the Gal-α(1→3)-Gal-pNP synthesis and increased the Gal-α(1→4)-Gal yield compared to Gal-α(1→6)-Gal-pNP.
Arabinogalactan hydrolysis and hydrolytic hydrogenation using functionalized carbon materials
Murzin, D.Yu.,Murzina,Tokarev,Shcherban,W?rn?,Salmi
, p. 169 - 176 (2015/02/19)
Hydrolysis of the hemicellulose arabinogalactan was studied in this work over several functionalized carbon materials, which were specifically treated to increase their acidities. Hydrolytic hydrogenation of arabinogalactan was investigated using the same materials in a mechanical mixture with ruthenium supported on active carbon. Application of these mixtures resulted in formation of polyols, suppressing simultaneously the generation of side products hydroxymethylfurfural (HMF) and furfural. Formation of high molecular weight compounds (aggregates of sugars and humins) was still quite substantial with a mechanical mixture of Ru/C and a carbon material prepared from sucrose by activation with zinc chloride to increase porosity. Post-treatment of this carbonaceous material with sulphuric acid significantly influenced kinetics of high molecular weight products formation resulting also in elevation of sugar alcohols yields.
α-Galactobiosyl units: Thermodynamics and kinetics of their formation by transglycosylations catalysed by the GH36 α-galactosidase from Thermotoga maritima
Borisova, Anna S.,Ivanen, Dina R.,Bobrov, Kirill S.,Eneyskaya, Elena V.,Rychkov, Georgy N.,Sandgren, Mats,Kulminskaya, Anna A.,Sinnott, Michael L.,Shabalin, Konstantin A.
supporting information, p. 115 - 121 (2015/02/19)
Broad regioselectivity of α-galactosidase from Thermotoga maritima (TmGal36A) is a limiting factor for application of the enzyme in the directed synthesis of oligogalactosides. However, this property can be used as a convenient tool in studies of thermodynamics of a glycosidic bond. Here, a novel approach to energy difference estimation is suggested. Both transglycosylation and hydrolysis of three types of galactosidic linkages were investigated using total kinetics of formation and hydrolysis of pNP-galactobiosides catalysed by monomeric glycoside hydrolase family 36 α-galactosidase from T. maritima, a retaining exo-acting glycoside hydrolase. We have estimated transition state free energy differences between the 1,2- and 1,3-linkage (ΔΔG?0 values were equal 5.34 ± 0.85 kJ/mol) and between 1,6-linkage and 1,3-linkage (ΔΔG?0 = 1.46 ± 0.23 kJ/mol) in pNP-galactobiosides over the course of the reaction catalysed by TmGal36A. Using the free energy difference for formation and hydrolysis of glycosidic linkages (ΔΔG?F - ΔΔG?H), we found that the 1,2-linkage was 2.93 ± 0.47 kJ/mol higher in free energy than the 1,3-linkage, and the 1,6-linkage 4.44 ± 0.71 kJ/mol lower.
The method of integrated kinetics and its applicability to the exo-glycosidase-catalyzed hydrolyses of p-nitrophenyl glycosides
Borisova, Anna S.,Reddy, Sumitha K.,Ivanen, Dina R.,Bobrov, Kirill S.,Eneyskaya, Elena V.,Rychkov, Georgy N.,Sandgren, Mats,St?lbrand, Henrik,Sinnott, Michael L.,Kulminskaya, Anna A.,Shabalin, Konstantin A.
, p. 43 - 49 (2015/06/02)
In the present work we suggest an efficient method, using the whole time course of the reaction, whereby parameters kcat, Km and product KI for the hydrolysis of a p-nitrophenyl glycoside by an exo-acting glycoside hydrola
Evaluating binuclear copper(II) complexes for glycoside hydrolysis
Striegler, Susanne,Dunaway, Natasha A.,Gichinga, Moses G.,Barnett, James D.,Nelson, Anna-Gay D.
experimental part, p. 2639 - 2648 (2010/06/20)
Three binuclear copper(II) complexes were characterized as solids by X-ray diffraction and in solution by UV/vis spectrophotometric titration, and subsequently evaluated for their glycosidase-like activity. The structure analysis revealed comparable intermetallic Cu ? ? ? Cu distances (~3.5 A) for the complexes 2 and 3. Despite this similarity, the composition of the complexes differs significantly in aqueous solution as revealed by spectrophotometric titrations. The hydrolysis of selected nitrophenylglycopyranosides is up to 11,000-fold accelerated over background in the presence of the copper(II) complexes in 3-(cyclohexylamino)-1- propanesulfonic acid (CAPS) buffer at pH 10.5 and 30 °C.
A mild, highly efficient, and chemoselective deprotection of trityl ethers of carbohydrates and nucleosides using iodine monobromide
Malik, Satish,Kartha, K. P. Ravindranathan
body text, p. 1809 - 1811 (2009/12/04)
Iodine monobromide in dichloromethane-methanol or acetonitrile constitutes an effective reagent for the deprotection of O-trityl and O-dimethoxytrityl ethers of carbohydrates and nucleosides. Acid-labile functionalities (acetals, O-p-methoxybenzyl ethers, etc.) as well as base-labile groups (esters and amides) are stable under these conditions; and the method has been found to be superior to the hitherto known literature methods. Georg Thieme Verlag Stuttgart.
APPLICATIONS OF BIOBASED GLYCOL COMPOSITIONS
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Page/Page column 11, (2008/06/13)
A biobased replacement for propylene glycol and ethylene glycol derived from petrochemical sources is presented. The product mixture from the hydrogenolysis of certain polyols from biobased renewable resources may replace propylene glycol and ethylene glycol products from petrochemical sources. Applications and methods of the biobased hydrogenolysis product mixture are disclosed. The compositions and methods provide a feedstock for industrial use which has a 13C/12C isotope ratio characteristic of bioderived material.
