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Found 1 structure.
Displayed structure 1
| -4)-b-D-GlcpN6Ac-(1- | Show graphically |
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Structure type: homopolymer
Trivial name: chitin
Contained glycoepitopes: IEDB_141807,IEDB_151531
Chitin is a polymer of N-acetylglucosamine, which assembles into microfibrils of about 20 sugar chains. These microfibrils serve as a structural component of natural biocomposites found in cell walls and specialized extracellular matrices such as cuticles and peritrophic membranes. Chitin synthesis is performed by a wide range of organisms including fungi and insects. The underlying biosynthetic machinery is highly conserved and involves several enzymes, of which the chitin synthase is the key enzyme. This membrane integral glycosyltransferase catalyzes the polymerization reaction. Most of what we know about chitin synthesis derives from studies of fungal and insect systems. In this review, common principles and differences will be worked out at the levels of gene organization, enzymatic properties, cellular localization and regulation.
cell wall, glycosyltransferase, chitin, chitin synthase, Chitin metabolism, Cuticle, Peritrophic matrix
NCBI PubMed ID: 21700357Chitin synthases polymerize UDP-GlcNAC to form chitin polymer, a key component of fungal cell wall biosynthesis. Furthermore, chitin synthases are desirable targets for fungicides since chitin is absent in plants and mammals. Two potent Botrytis cinerea chitin synthase inhibitors, 2,3,5-tri-O-benzyl-d-ribose (compound 1) and a 2,5-functionalized imidazole (compound 2) were identified by screening a chemical library. We adapted the wheat germ agglutinin (WGA) test for chitin synthase activity detection to allow miniaturization and robotization of the screen. Both identified compounds inhibited chitin synthases in vitro with IC50 values of 1.8 and 10μM, respectively. Compounds 1 and 2 were evaluated for their antifungal activity and were found to be active against B. cinerea BD90 strain with MIC values of 190 and 100μM, respectively. Finally, we discovered that both compounds confer resistance to plant leaves against the attack of the fungus by reducing the propagation of lesions by 37% and 23%, respectively. Based on the inhibitory properties found in different assays, compounds 1 and 2 can be considered as antifungal hit inhibitors of chitin synthase, allowing further optimization of their pharmacological profile to improve their antifungal properties.
glycosyltransferase, inhibitor, chitin synthase, Botrytis cinerea, antifungal compounds
NCBI PubMed ID: 23886809Cork, the outer bark of Quercus suber, shows a unique compositional structure, a set of remarkable properties, including high recalcitrance. Cork colonisation by Ascomycota remains largely overlooked. Herein, Aspergillus nidulans secretome on cork was analysed (2DE). Proteomic data were further complemented by microscopic (SEM) and spectroscopic (ATR-FTIR) evaluation of the colonised substrate and by targeted analysis of lignin degradation compounds (UPLC-HRMS). Data showed that the fungus formed an intricate network of hyphae around the cork cell walls, which enabled polysaccharides and lignin superficial degradation, but probably not of suberin. The degradation of polysaccharides was suggested by the identification of few polysaccharide degrading enzymes (β-glucosidases and endo-1,5-α-l-arabinosidase). Lignin degradation, which likely evolved throughout a Fenton-like mechanism relying on the activity of alcohol oxidases, was supported by the identification of small aromatic compounds (e.g. cinnamic acid and veratrylaldehyde) and of several putative high molecular weight lignin degradation products. In addition, cork recalcitrance was corroborated by the identification of several protein species which are associated with autolysis. Finally, stringent comparative proteomics revealed that A. nidulans colonisation of cork and wood share a common set of enzymatic mechanisms. However the higher polysaccharide accessibility in cork might explain the increase of β-glucosidase in cork secretome. BIOLOGICAL SIGNIFICANCE: Cork degradation by fungi remains largely overlook. Herein we aimed at understanding how A. nidulans colonise cork cell walls and how this relates to wood colonisation. To address this, the protein species consistently present in the secretome were analysed, as well as major alterations occurring in the substrate, including lignin degradation compounds being released. The obtained data demonstrate that this fungus has superficially attacked the cork cell walls apparently by using both enzymatic and Fenton-like reactions. Only a few polysaccharide degrading enzymes could be detected in the secretome which was dominated by protein species associated with autolysis. Lignin degradation was corroborated by the identification of some degradation products, but the suberin barrier in the cell wall remained virtually intact. Comparative proteomics revealed that cork and wood colonisation share a common set of enzymatic mechanisms.
secretome, Aspergillus nidulans, alcohol oxidase, cork, fenton-like reactions, lignin degradation
NCBI PubMed ID: 24316358The innate immune system constitutes the first line of defence against invading microbes. The basis of this defence resides in the recognition of defined structural motifs of the microbes called "Microbial associated molecular patterns" that are absent in the host. Cell wall, the outer layer of both bacterial and fungal cells, a unique structure that is absent in the host and is recognized by the germ line encoded host receptors. Nucleotide oligomerization domain proteins, peptidoglycan recognition proteins and C-type lectins are host receptors that are involved in the recognition of bacterial cell wall (usually called peptidoglycan), whereas fungal cell wall components (N- and O-linked mannans, β-glucans etc.) are recognized by host receptors like C-type lectins (Dectin-1, Dectin-2, mannose receptor, DC-SIGN), Toll like receptors-2 and -4 (TLR-2 and TLR-4). These recognitions lead to activation of a variety of host signaling cascades and ultimate production of anti-microbial compounds including phospholipase A2, antimicrobial peptides, lysozyme, reactive oxygen and nitrogen species. These molecules act in cohort against the invading microbes to eradicate infections. Additionally pathogen recognition leads to the production of cytokines, which further activate the adaptive immune system. Both pathogenic and commensal bacteria and fungus use numerous strategies to subvert the host defence. These strategies include bacterial peptidoglycan glycan backbone modifications by O-acetylation, N-deacetylation, N-glycolylation and stem peptide modifications by amidation of meso-Diaminopimelic acid; fungal cell wall modifications by shielding the β-glucan layer with mannoproteins and α-1,3 glucan. This review focuses on the recent advances in understanding the role of bacterial and fungal cell wall in their innate immune recognition and evasion strategies.
NCBI PubMed ID: 23578963The structural carbohydrate polymers glucan and chitin compliment and reinforce each other in a dynamic process to maintain the integrity and physical strength of the fungal cell wall. The assembly of chitin and glucan in the cell wall of the budding yeast Saccharomyces cerevisiae and the polymorphic human pathogen Candida albicans are essential processes that involve a range of fungal-specific enzymes and regulatory networks. The fungal cell wall is, therefore, an attractive target for novel therapies as host cells lack many cell wall-related proteins. The most recent class of antifungal drug approved for clinical use, the echinocandins, targets the synthesis of cell wall β(1-3)glucan. The echinocandins are effective at treating invasive and bloodstream Candida infections and are now widely used in the clinic. However, there have been sporadic reports of breakthrough infections in patients undergoing echinocandin therapy. The acquisition of point mutations in the FKS genes that encode the catalytic β(1-3)glucan synthase subunits, the target of the echinocandins, has emerged as a dominant resistance mechanism. Cells with elevated chitin levels are also less susceptible to echinocandins and in addition, treatment with sub-MIC echinocandin activates cell wall salvage pathways that increase chitin synthesis to compensate for reduced glucan production. The development of drugs targeting the cell wall has already proven to be beneficial in providing an alternative class of drug for use in the clinic. Other cell wall targets such as chitin synthesis still hold great potential for drug development but careful consideration should be given to the capacity of fungi to manipulate their walls in a dynamic response to cell wall perturbations.
glucan, chitin, fungal cell wall
NCBI PubMed ID: 23651596Background: Cell wall of Malassezia restricta is involved in interactions with human skin. Results: Its core is composed of cross-linked polysaccharides such as chitin, chitosan, α-(1,3)-glucan and α-(1,6)-glucan. Conclusion: The composition of cell wall polysaccharides of M. restricta is unique in the fungal kingdom. Significance: The cell wall of M. restricta has evolved as a yeast that adapted to the skin microenvironment and host interactions.
cell wall
NCBI PubMed ID: 24627479Plants are sessile organisms that are under constant attack from microbes. They rely on both preformed defenses, and their innate immune system to ward of the microbial pathogens. Preformed defences include for example the cell wall and cuticle, which act as physical barriers to microbial colonization. The plant immune system is composed of surveillance systems that perceive several general microbe elicitors, which allow plants to switch from growth and development into a defense mode, rejecting most potentially harmful microbes. The elicitors are essential structures for pathogen survival and are conserved among pathogens. The conserved microbe-specific molecules, referred to as microbe- or pathogen-associated molecular patterns (MAMPs or PAMPs), are recognized by the plant innate immune systems pattern recognition receptors (PRRs). General elicitors like flagellin (Flg), elongation factor Tu (EF-Tu), peptidoglycan (PGN), lipopolysaccharides (LPS), Ax21 (Activator of XA21-mediated immunity in rice), fungal chitin, and β-glucans from oomycetes are recognized by plant surface localized PRRs. Several of the MAMPs and their corresponding PRRs have, in recent years, been identified. This review focuses on the current knowledge regarding important MAMPs from bacteria, fungi, and oomycetes, their structure, the plant PRRs that recognizes them, and how they induce MAMP-triggered immunity (MTI) in plants.
LPS, innate immunity, MAMPs, Ax21, сhitin, EF-Tu, Flg22, PGN
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