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Laminaritriose

Laminaritriose O-LAM3
Product code: O-LAM3
€220.00

50 mg

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Content: 50 mg
Shipping Temperature: Ambient
Storage Temperature: Ambient
Physical Form: Powder
Stability: > 2 years under recommended storage conditions
CAS Number: 3256-04-0
Molecular Formula: C18H32O16
Molecular Weight: 504.4
Purity: > 95%
Substrate For (Enzyme): endo-1,3-β-Glucanase

High purity Laminaritriose for use in research, biochemical enzyme assays and in vitro diagnostic analysis.

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Certificate of Analysis
Safety Data Sheet
Data Sheet
Publications
Megazyme publication

Versatile high resolution oligosaccharide microarrays for plant glycobiology and cell wall research.

Pedersen, H. L., Fangel, J. U., McCleary, B., Ruzanski, C., Rydahl, M. G., Ralet, M. C., Farkas, V., Von Schantz, L., Marcus, S. E., Andersen, M.C. F., Field, R., Ohlin, M., Knox, J. P., Clausen, M. H. & Willats, W. G. T. (2012). Journal of Biological Chemistry, 287(47), 39429-39438.

Microarrays are powerful tools for high throughput analysis, and hundreds or thousands of molecular interactions can be assessed simultaneously using very small amounts of analytes. Nucleotide microarrays are well established in plant research, but carbohydrate microarrays are much less established, and one reason for this is a lack of suitable glycans with which to populate arrays. Polysaccharide microarrays are relatively easy to produce because of the ease of immobilizing large polymers noncovalently onto a variety of microarray surfaces, but they lack analytical resolution because polysaccharides often contain multiple distinct carbohydrate substructures. Microarrays of defined oligosaccharides potentially overcome this problem but are harder to produce because oligosaccharides usually require coupling prior to immobilization. We have assembled a library of well characterized plant oligosaccharides produced either by partial hydrolysis from polysaccharides or by de novo chemical synthesis. Once coupled to protein, these neoglycoconjugates are versatile reagents that can be printed as microarrays onto a variety of slide types and membranes. We show that these microarrays are suitable for the high throughput characterization of the recognition capabilities of monoclonal antibodies, carbohydrate-binding modules, and other oligosaccharide-binding proteins of biological significance and also that they have potential for the characterization of carbohydrate-active enzymes.

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Publication

Quantitation of bioactive components in infant formulas: Milk oligosaccharides, sialic acids and corticosteroids.

Liu, F., van der Molen, J., Kuipers, F. & van Leeuwen, S. S. (2023). Food Research International, 174, 113589.

Human milk is considered the optimal food for infants with abundant nutrients and bioactive components, which play key roles in infant health and development. Infant formulas represent appropriate substitutes for human milk. There are many brands of infant formula with different ingredient sources and functions on the market. The present study aims to quantify important bioactive components, i.e., milk oligosaccharides (MOS), sialic acids (Sia) and corticosteroids, in different infant formulas and compare these to human milk. In total, 12 different infant formulas available on the Dutch market were analyzed in this study. The concentrations of MOS and Sia were characterized by UHPLC-FLD and LC-MS, while corticosteroids were determined using established UHPLC-MS/MS methods. Among infant formulas, 15 structures of oligosaccharides were identified, of which 2′-Fucosyllactose (2′FL), 3′-Galactosyllactose (3′GL) and 6′-Galactosyllactose (6́′GL) were found in all infant formulas. The oligosaccharide concentrations differed between milk source and brands and were 3–5 times lower than in human milk. All infant formulas contained Sia, N-acetylneuraminic acid (Neu5Ac) was dominant in bovine milk-based formulas, while N-glycolylneuraminic acid (Neu5Gc) was major in goat milk-based formula. All infant formulas contained corticosteroids, yet, at lower concentrations than human milk. Insight in concentrations of bioactive components in infant formula compared to human milk may give direction to dietary advices and/or novel formula design.

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Plant immunity suppression by an exo-β-1, 3-glucanase and an elongation factor 1α of the rice blast fungus. 

Liu, H., Lu, X., Li, M., Lun, Z., Yan, X., Yin, C., .et al. (2023). Nature Communications, 14(1), 5491.

Fungal cell walls undergo continual remodeling that generates β-1,3-glucan fragments as products of endo-glycosyl hydrolases (GHs), which can be recognized as pathogen-associated molecular patterns (PAMPs) and trigger plant immune responses. How fungal pathogens suppress those responses is often poorly understood. Here, we study mechanisms underlying the suppression of β-1,3-glucan-triggered plant immunity by the blast fungus Magnaporthe oryzae. We show that an exo-β-1,3-glucanase of the GH17 family, named Ebg1, is important for fungal cell wall integrity and virulence of M. oryzae. Ebg1 can hydrolyze β-1,3-glucan and laminarin into glucose, thus suppressing β-1,3-glucan-triggered plant immunity. However, in addition, Ebg1 seems to act as a PAMP, independent of its hydrolase activity. This Ebg1-induced immunity appears to be dampened by the secretion of an elongation factor 1 alpha protein (EF1α), which interacts and co-localizes with Ebg1 in the apoplast. Future work is needed to understand the mechanisms behind Ebg1-induced immunity and its suppression by EF1α.

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New colours for old in the blue-cheese fungus Penicillium roqueforti.

Cleere, M. M., Novodvorska, M., Geib, E., Whittaker, J., Dalton, H., Salih, N., Hewitt, S., Kokolski, M. Brock, M. & Dyer, P. S. (2024). npj Science of Food, 8(1), 3.

Penicillium roqueforti is used worldwide in the production of blue-veined cheese. The blue-green colour derives from pigmented spores formed by fungal growth. Using a combination of bioinformatics, targeted gene deletions, and heterologous gene expression we discovered that pigment formation was due to a DHN-melanin biosynthesis pathway. Systematic deletion of pathway genes altered the arising spore colour, yielding white to yellow-green to red-pink-brown phenotypes, demonstrating the potential to generate new coloured strains. There was no consistent impact on mycophenolic acid production as a result of pathway interruption although levels of roquefortine C were altered in some deletants. Importantly, levels of methyl-ketones associated with blue-cheese flavour were not impacted. UV-induced colour mutants, allowed in food production, were then generated. A range of colours were obtained and certain phenotypes were successfully mapped to pathway gene mutations. Selected colour mutants were subsequently used in cheese production and generated expected new colourations with no elevated mycotoxins, offering the exciting prospect of use in future cheese manufacture.

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Utilization of dietary mixed-linkage β-glucans by the Firmicute Blautia producta.

Singh, R. P., Niharika, J., Thakur, R., Wagstaff, B. A., Kumar, G., Kurata, R., Patel, D., Levy, C. W., Miyazaki, T. & Field, R. A. (2023). Journal of Biological Chemistry, 299(6).

The β-glucans are structurally varied, naturally occurring components of the cell walls, and storage materials of a variety of plant and microbial species. In the human diet, mixed-linkage glucans [MLG - β-(1,3/4)-glucans] influence the gut microbiome and the host immune system. Although consumed daily, the molecular mechanism by which human gut Gram-positive bacteria utilize MLG largely remains unknown. In this study, we used Blautia producta ATCC 27340 as a model organism to develop an understanding of MLG utilization. B. producta encodes a gene locus comprising a multi-modular cell-anchored endo-glucanase (BpGH16MLG), an ABC transporter, and a glycoside phosphorylase (BpGH94MLG) for utilizing MLG, as evidenced by the upregulation of expression of the enzyme- and solute binding protein (SBP)-encoding genes in this cluster when the organism is grown on MLG. We determined that recombinant BpGH16MLG cleaved various types of β-glucan, generating oligosaccharides suitable for cellular uptake by B. producta. Cytoplasmic digestion of these oligosaccharides is then performed by recombinant BpGH94MLG and β-glucosidases (BpGH3-AR8MLG and BpGH3-X62MLG). Using targeted deletion, we demonstrated BpSBPMLG is essential for B. producta growth on barley β-glucan. Furthermore, we revealed that beneficial bacteria, such as Roseburia faecis JCM 17581T, Bifidobacterium pseudocatenulatum JCM 1200T, Bifidobacterium adolescentis JCM 1275T, and Bifidobacterium bifidum JCM 1254, can also utilize oligosaccharides resulting from the action of BpGH16MLG. Disentangling the β-glucan utilizing the capability of B. producta provides a rational basis on which to consider the probiotic potential of this class of organism.

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Structural identification of carbohydrate isomers using ambient infrared-assisted dissociation.

Lai, Y. H., Leung, W., Chang, P. H., Zhou, W. X. & Wang, Y. S. (2023). Analytica Chimica Acta, 1264, 341307.

Informative dissociation of carbohydrates using an infrared (IR) irradiation system is demonstrated under ambient conditions without the instrumentation of a mass spectrometer. Structural identification of carbohydrates and associated conjugates is essential for understanding their biological functions, but identification remains challenging. Herein, an easy and rugged method is reported for the structural identification of model carbohydrates, including Globo-H, three trisaccharide isomers (nigerotriose/laminaritriose/cellotriose), and two hexasaccharide isomers (laminarihexaose/isomaltohexaose). For Globo-H, the numbers of cross-ring cleavages increased by factors of 4.4 and 3.4 upon ambient IR exposure, compared to an untreated control and a collision-induced dissociation (CID) sample. Moreover, 25-82% enhancement in the numbers of glycosidic bond cleavages upon ambient IR exposure was also obtained compared to untreated and CID samples. Unique features of first-generation fragments produced by ambient IR facilitated the differentiation of three trisaccharide isomers. Semi-quantitative analysis was achieved (coefficient of determination (R2) of 0.982) in a mixture of two hexasaccharide isomers via unique features generated upon ambient IR. Photothermal and radical migration effects induced by ambient IR were postulated as responsible for promoting carbohydrate fragmentation. This easy and rugged method could be a universally applicable protocol and complementary to other techniques for detailed structural characterization of carbohydrates.

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Structural and mechanistic insights into fungal β-1, 3-glucan synthase FKS1.

Hu, X., Yang, P., Chai, C., Liu, J., Sun, H., Wu, Y., Zhang, M., Zhang, M, Liu, X. & Yu, H. (2023). Nature, 38, 1-9.

The membrane-integrated synthase FKS is involved in the biosynthesis of β-1,3-glucan, the core component of the fungal cell wall. FKS is the target of widely prescribed antifungal drugs, including echinocandin and ibrexafungerp. Unfortunately, the mechanism of action of FKS remains enigmatic and this has hampered development of more effective medicines targeting the enzyme. Here we present the cryo-electron microscopy structures of Saccharomyces cerevisiae FKS1 and the echinocandin-resistant mutant FKS1(S643P). These structures reveal the active site of the enzyme at the membrane-cytoplasm interface and a glucan translocation path spanning the membrane bilayer. Multiple bound lipids and notable membrane distortions are observed in the FKS1 structures, suggesting active FKS1-membrane interactions. Echinocandin-resistant mutations are clustered at a region near TM5-6 and TM8 of FKS1. The structure of FKS1(S643P) reveals altered lipid arrangements in this region, suggesting a drug-resistant mechanism of the mutant enzyme. The structures, the catalytic mechanism and the molecular insights into drug-resistant mutations of FKS1 revealed in this study advance the mechanistic understanding of fungal β-1,3-glucan biosynthesis and establish a foundation for developing new antifungal drugs by targeting FKS.

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Poaceae-specific cell wall-derived oligosaccharides activate plant immunity via OsCERK1 during Magnaporthe oryzae infection in rice.

Yang, C., Liu, R., Pang, J., Ren, B., Zhou, H., Wang, G., wang, E. & Liu, J. (2021). Nature Communications, 12(1), 1-13.

Many phytopathogens secrete cell wall degradation enzymes (CWDEs) to damage host cells and facilitate colonization. As the major components of the plant cell wall, cellulose and hemicellulose are the targets of CWDEs. Damaged plant cells often release damage-associated molecular patterns (DAMPs) to trigger plant immune responses. Here, we establish that the fungal pathogen Magnaporthe oryzae secretes the endoglucanases MoCel12A and MoCel12B during infection of rice (Oryza sativa). These endoglucanases target hemicellulose of the rice cell wall and release two specific oligosaccharides, namely the trisaccharide 31-β-D-Cellobiosyl-glucose and the tetrasaccharide 31-β-D-Cellotriosyl-glucose. 31-β-D-Cellobiosyl-glucose and 31-β-D-Cellotriosyl-glucose bind the immune receptor OsCERK1 but not the chitin binding protein OsCEBiP. However, they induce the dimerization of OsCERK1 and OsCEBiP. In addition, these Poaceae cell wall-specific oligosaccharides trigger a burst of reactive oxygen species (ROS) that is largely compromised in oscerk1 and oscebip mutants. We conclude that 31-β-D-Cellobiosyl-glucose and 31-β-D-Cellotriosyl-glucose are specific DAMPs released from the hemicellulose of rice cell wall, which are perceived by an OsCERK1 and OsCEBiP immune complex during M. oryzae infection in rice.

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A maizewin protein confers enhanced antiinsect and antifungal resistance when the gene is transgenically expressed in maize callus.

Dowd, P. F., Naumann, T. A., Johnson, E. T. & Price, N. P. (2020). Plant Gene, 24, 100259.

Maize is a crop of worldwide importance, but insects and plant pathogens limit sustainable production. The development of maize varieties with improved resistance will be facilitated by identification of relevant resistance alleles through appropriate biological assays. A barwin-like gene (which we call maizewin) located in a QTL for Fusarium resistance annotated such that potential glucanase and chitinase activity could occur in the translated protein, was cloned from an ear rot resistant inbred and transgenically expressed in maize callus. Although limited increases in insect resistance occurred in the transgenic callus material containing the maizewin gene compared to a GUS control gene, resistance to Fusarium pathogens was common and associated with increased glucanase activity. The gene appeared to produce a protein with glucanase and chitosanase activity, consistent with an antifungal role. The allele that produces the functional resistant protein may be relatively uncommon in maize germplasm. Incorporation of a functional maizewin allele into susceptible germplasm should help increase production by contributing to control of both insect pests and plant pathogens.

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Synergistic immunomodulatory effect of complex polysaccharides from seven herbs and their major active fractions.

Deng, Y., Xie, J., Luo, Z., Li, S. P. & Zhao, J. (2020). International Journal of Biological Macromolecules, 165, 530-541.

In this report, we present the strategy for the revelation of synergistic effect and elucidation of active fractions from an immunomodulatory complex polysaccharide derived from seven herbs (Lentinula edodes, Ganodorma lucidum, Tremella fuciformis, Chrysanthemum, Lycium barbarum, Codonopsis pilosula and Poria cocos), a formula used as health product in China market, using the combination of HPSEC-MALLS, immunological bioassay and saccharide mapping analysis. The effects of complex polysaccharide and their fractions on RAW 246.7 macrophages demonstrated that the fractions (CD1, CD2, CD3) with molecular weight above 10 kDa exhibited immune activity by directly stimulated NO release and phagocytosis, and induced macrophages to secrete cytokines. Especially, fraction CD2 with molecular weight of 100-1000 kDa showed the strongest bioactivity (EC50 = 0.19 μg/mL) compared with their individual corresponding herbal polysaccharides fractions due to synergistic effect, which supported the scientific use of Chinese herbal mixture. Moreover, their chemical characters were analyzed by HPSEC-MALLS and saccharide mapping, and the original herbs, including L. edodes, G. lucidum, T. fuciformis and Chrysanthemum, responsible for the immunomodulatory activity were tentatively revealed. Results are beneficial for the quality analysis and formula optimization of complex polysaccharides in both biomedical and functional food field.

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Safety Data Sheet
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