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Applied Microbiology and Biotechnology Oct 2019Glucosamine (GlcN) is an amine sugar, in which a hydroxyl group of glucose is replaced with an amino group. It is an important part of the polysaccharides chitin and... (Review)
Review
Glucosamine (GlcN) is an amine sugar, in which a hydroxyl group of glucose is replaced with an amino group. It is an important part of the polysaccharides chitin and chitosan and is highly hydrophilic. It is also an important compound required for the formation of cartilage cells and represents one of the elementary units of the cartilage matrix and joint fluid. GlcN has been widely used in food, cosmetics, health care, and pharmaceutical industries. This paper fully addresses the categories and biomanufacturing methods of GlcN, including its production by fermentation with wild-type as well as engineered microorganisms and enzymatic catalysis with a series of chitinolytic enzymes. However, GlcN is usually produced from glucose by fermentation in a coupled manner with N-acetylglucosamine (GlcNAc). Enzymatic catalysis is thus a specific pathway for production of GlcN where chitin can be directly hydrolyzed to GlcN. In industry, GlcN produced with fungal mycelium as raw materials (plant GlcN) is thought as a high-end product because of vegetarian and non-transgenosis. In our opinion, more studies should be performed in order to develop a competitive enzymatic pathway using Aspergillus niger mycelium for the preparation of high-end GlcN.
Topics: Aspergillus niger; Biocatalysis; Fermentation; Glucosamine; Industrial Microbiology; Metabolic Networks and Pathways; Mycelium
PubMed: 31440792
DOI: 10.1007/s00253-019-10084-x -
Biomaterials Science Apr 2023Sialic acid is a kind of monosaccharide expressed on the non-reducing end of glycoproteins or glycolipids. It acts as a signal molecule combining with its natural... (Review)
Review
Sialic acid is a kind of monosaccharide expressed on the non-reducing end of glycoproteins or glycolipids. It acts as a signal molecule combining with its natural receptors such as selectins and siglecs (sialic acid-binding immunoglobulin-like lectins) in intercellular interactions like immunological surveillance and leukocyte infiltration. The last few decades have witnessed the exploration of the roles that sialic acid plays in different physiological and pathological processes and the use of sialic acid-modified materials as therapeutics for related diseases like immune dysregulation and virus infection. In this review, we will briefly introduce the biomedical function of sialic acids in organisms and the utilization of multivalent sialic acid materials for targeted drug delivery as well as therapeutic applications including anti-inflammation and anti-virus.
Topics: N-Acetylneuraminic Acid; Sialic Acid Binding Immunoglobulin-like Lectins; Sialic Acids; Glycoproteins; Leukocytes
PubMed: 36661319
DOI: 10.1039/d2bm01595a -
Molecules (Basel, Switzerland) Mar 2018Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks... (Review)
Review
Nucleic acids and carbohydrates are essential biomolecules involved in numerous biological and pathological processes. Development of multifunctional building blocks based on nucleosides and sugars is in high demand for the generation of novel oligonucleotide mimics and glycoconjugates for biomedical applications. Recently, aminooxyl-functionalized compounds have attracted increasing research interest because of their easy derivatization through oxime ligation or -oxyamide formation reactions. Various biological applications have been reported for -amino carbohydrate- and nucleoside-derived compounds. Here, we report our efforts in the design and synthesis of glyco-, glycosyl, nucleoside- and nucleo-aminooxy acid derivatives from readily available sugars and amino acids, and their use for the generation of -oxyamide-linked oligosaccharides, glycopeptides, glycolipids, oligonucleosides and nucleopeptides as novel glycoconjugates or oligonucleotide mimics. Delicate and key points in the synthesis will be emphasized.
Topics: Amino Sugars; Molecular Structure; Nucleosides; Oximes
PubMed: 29534554
DOI: 10.3390/molecules23030641 -
BMC Biology Jul 2019Altered metabolism and deregulated cellular energetics are now considered a hallmark of all cancers. Glucose, glutamine, fatty acids, and amino acids are the primary... (Review)
Review
Altered metabolism and deregulated cellular energetics are now considered a hallmark of all cancers. Glucose, glutamine, fatty acids, and amino acids are the primary drivers of tumor growth and act as substrates for the hexosamine biosynthetic pathway (HBP). The HBP culminates in the production of an amino sugar uridine diphosphate N-acetylglucosamine (UDP-GlcNAc) that, along with other charged nucleotide sugars, serves as the basis for biosynthesis of glycoproteins and other glycoconjugates. These nutrient-driven post-translational modifications are highly altered in cancer and regulate protein functions in various cancer-associated processes. In this review, we discuss recent progress in understanding the mechanistic relationship between the HBP and cancer.
Topics: Biosynthetic Pathways; Hexosamines; Neoplasms; Protein Processing, Post-Translational; Proteins
PubMed: 31272438
DOI: 10.1186/s12915-019-0671-3 -
Advances in Carbohydrate Chemistry and... 2022The synthesis of sialic acid-containing molecules has posed a formidable challenge to carbohydrate chemists for over 50 years. Our research group has intensively...
The synthesis of sialic acid-containing molecules has posed a formidable challenge to carbohydrate chemists for over 50 years. Our research group has intensively searched for robust chemistry to enable the construction of a broad spectrum of sialic acid-containing molecules to advance the understanding and application of their biological functions. Herein, we describe our research findings on the development of sialic acid donors for α-selective glycosidation and the chemical synthesis of sialic acid- containing molecules, with a special focus on gangliosides and their fluorescent probes.
Topics: Sialic Acids; N-Acetylneuraminic Acid; Gangliosides; Carbohydrates; Fluorescent Dyes
PubMed: 36435533
DOI: 10.1016/bs.accb.2022.09.003 -
Molecular Oral Microbiology Apr 2018Tannerella forsythia is a Gram-negative oral pathogen strongly associated with periodontitis. This bacterium has an absolute requirement for exogenous N-acetylmuramic... (Review)
Review
Tannerella forsythia is a Gram-negative oral pathogen strongly associated with periodontitis. This bacterium has an absolute requirement for exogenous N-acetylmuramic acid (MurNAc), an amino sugar that forms the repeating disaccharide unit with amino sugar N-acetylglucosamine (GlcNAc) of the peptidoglycan backbone. In silico genome analysis indicates that T. forsythia lacks the key biosynthetic enzymes needed for the de novo synthesis of MurNAc, and so relies on alternative ways to meet its requirement for peptidoglycan biosynthesis. In the subgingival niche, the bacterium can acquire MurNAc and peptidoglycan fragments (muropeptides) released by the cohabiting bacteria during their cell wall breakdown associated with cell division. Tannerella forsythia is able to also use host sialic acid (Neu5Ac) in lieu of MurNAc or muropeptides for its survival during the biofilm growth. Evidence suggests that the bacterium might be able to shunt sialic acid into a metabolic pathway leading to peptidoglycan synthesis. In this review, we explore the mechanisms by which T. forsythia is able to scavenge MurNAc, muropeptide and sialic acid for its peptidoglycan synthesis, and the impact of these scavenging activities on pathogenesis.
Topics: Acetylglucosamine; Biofilms; Cell Wall; Environment; Host-Pathogen Interactions; Metabolic Networks and Pathways; Muramic Acids; N-Acetylneuraminic Acid; Peptidoglycan; Periodontitis; Tannerella forsythia
PubMed: 29247483
DOI: 10.1111/omi.12210 -
Biotechnology Advances 2021Sialic acids (Sias) are negatively charged functional monosaccharides present in a wide variety of natural sources (plants, animals and microorganisms). Sias play an... (Review)
Review
Sialic acids (Sias) are negatively charged functional monosaccharides present in a wide variety of natural sources (plants, animals and microorganisms). Sias play an important role in many life processes, which are widely applied in the medical and food industries as intestinal antibacterials, antivirals, anti-oxidative agents, food ingredients, and detoxification agents. Most Sias are composed of N-acetylneuraminic acid (Neu5Ac, >99%), and Sia is its most commonly used name. In this article, we review Sias in terms of their structures, applications, determination methods, metabolism, and production strategies. In particular, we summarise and compare different production strategies, including extraction from natural sources, chemical synthesis, polymer decomposition, enzymatic synthesis, whole-cell catalysis, and de novo biosynthesis via microorganism fermentation. We also discuss research on their physiological functions and applications, barriers to efficient production, and strategies for overcoming these challenges. We focus on efficient de novo biosynthesis strategies for Neu5Ac via microbial fermentation using novel synthetic biology tools and methods that may be applied in future. This work provides a comprehensive overview of recent advances on Sias, and addresses future challenges regarding their functions, applications, and production.
Topics: Animals; N-Acetylneuraminic Acid; Sialic Acids; Synthetic Biology
PubMed: 33285252
DOI: 10.1016/j.biotechadv.2020.107678 -
Immunology Nov 2020Mounting an effective immune response is crucial for the host to protect itself against invading pathogens. It is now well appreciated that reprogramming of core... (Review)
Review
Mounting an effective immune response is crucial for the host to protect itself against invading pathogens. It is now well appreciated that reprogramming of core metabolic pathways in immune cells is a key requirement for their activation and function during infections. The role of several ancillary metabolic pathways in shaping immune cell function is less well understood. One such pathway, for which interest has recently been growing, is the hexosamine biosynthesis pathway (HBP) that generates uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), the donor substrate for a specific form of glycosylation termed O-GlcNAcylation. O-GlcNAc is an intracellular post-translational modification that alters the functional properties of the modified proteins, in particular transcription factors and epigenetic regulators. An increasing number of studies suggest a central role for the HBP and O-GlcNAcylation in dictating immune cell function, including the response to different pathogens. We here discuss the most recent insights regarding O-GlcNAcylation and immunity, and explore whether targeting of O-GlcNAcylation could hold promise as a therapeutic approach to modulate immune responses to infections.
Topics: Animals; Epigenesis, Genetic; Glucosamine; Glycosylation; Hexosamines; Humans; Immunity; Immunomodulation; Infections; beta-N-Acetylhexosaminidases
PubMed: 32740921
DOI: 10.1111/imm.13245 -
Journal of Natural Products Jun 2022Chemical investigation of Australian pasture plant-derived sp. CMB-PB041, supported by miniaturized cultivation profiling and molecular network analysis, led to the... (Review)
Review
Chemical investigation of Australian pasture plant-derived sp. CMB-PB041, supported by miniaturized cultivation profiling and molecular network analysis, led to the isolation and characterization of 13 new macrocyclic spirotetronates, glenthmycins A-M (-), with structures assigned by detailed spectroscopic analysis, chemical degradation and derivatization, and mechanistic and biosynthetic considerations. Hydrolysis of glenthmycin B () yielded the aglycone , whose structure and absolute configuration were secured by X-ray analysis, along with the unexpected amino sugar residues glenthose lactams A () and B (), with Mosher analysis of facilitating assignment of absolute configurations of the amino sugar. While the glenthmycins proved to be acid stable, treatment of isomeric glenthmycins (i.e., , , and ) with base catalyzed rapid intramolecular -esterification to regio-isomeric mixtures (i.e., + + ). Exposure of to base achieved the same intramolecular -esterification and was instrumental in detecting and tentatively identifying two additional minor co-metabolites, glenthmycins N () and O (). A structure-activity relationship analysis carried out on - and the semisynthetic analogues and - revealed a promising Gram +ve antibacterial pharmacophore, effective against methicillin-resistant (MRSA) and vancomycin-resistant Enterococci (VRE), but with no detectable cytotoxicity to eukaryotic cells (i.e., fungal and human carcinoma). Of particular note, the semisynthetic analogue glenthmycin K 9-valerate () was unique among glenthmycins in potently inhibiting growth of the full panel of Gram +ve pathogens (IC 0.2-1.6 μM). We conclude with an observation that any future evaluation of the antibacterial potential of glenthmycins and related macrocyclic spirotetronates may do well to include important soil-derived Gram +ve pathogens, such as , , and , the causative agents of anthrax, botulism, and livestock pneumonia.
Topics: Amino Sugars; Anthrax; Anti-Bacterial Agents; Australia; Humans; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Molecular Structure; Polyketides; Streptomyces
PubMed: 35640100
DOI: 10.1021/acs.jnatprod.2c00444 -
International Journal of Molecular... Sep 2022The interaction between selective nutrients and linked genes involving a specific organ reveals the genetic make-up of an individual in response to a particular... (Review)
Review
The interaction between selective nutrients and linked genes involving a specific organ reveals the genetic make-up of an individual in response to a particular nutrient. The interaction of genes with food opens opportunities for the addition of bioactive compounds for specific populations comprising identical genotypes. The slight difference in the genetic blueprints of humans is advantageous in determining the effect of nutrients and their metabolism in the body. The basic knowledge of emerging nutrigenomics and nutrigenetics can be applied to optimize health, prevention, and treatment of diseases. In addition, nutrient-mediated pathways detecting the cellular concentration of nutrients such as sugars, amino acids, lipids, and metabolites are integrated and coordinated at the organismal level via hormone signals. This review deals with the interaction of nutrients with various aspects of nutrigenetics and nutrigenomics along with pathways involved in nutrient sensing and regulation, which can provide a detailed understanding of this new leading edge in nutrition research and its potential application to dietetic practice.
Topics: Amino Sugars; Diet; Hormones; Humans; Lipids; Nutrients; Nutrigenomics; Perception
PubMed: 36232603
DOI: 10.3390/ijms231911305