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SLAS Technology Aug 2020
Topics: Carbohydrates; Glycomics; Monosaccharides; Proteins
PubMed: 32689910
DOI: 10.1177/2472630320937003 -
Small (Weinheim An Der Bergstrasse,... Sep 2021Unique supermolecular structures as chiral and flower-like microparticles and the precise tuning of the morphologies hold immense promise for a variety of applications....
Unique supermolecular structures as chiral and flower-like microparticles and the precise tuning of the morphologies hold immense promise for a variety of applications. Examples of such structures deriving from monosaccharides are still rare, and a general understanding is also lacking. Herein, it is shown that chiral, flower-like, or solid microparticles can be tuned by only using monosaccharide esters without external stimuli. Chiral "left-handed" (counterclockwise) and "right-handed" (clockwise) morphologies can be induced by d- and l-glucose stearoyl esters. In comparison, other monosaccharides, i.e., galactose, mannose, and xylose, cannot formed chiral particles and generated diverse other morphologies of the supermolecular microparticles based on their distinct molecular configurations. Due to the numbers of side chains and the bond orientations, microparticles with solid and porous flower-like morphologies can be obtained. While glucose and xylose esters only lead to solid microparticles, mannose and galactose generate porous flower-like particles. These findings suggest a general method to design and control the superstructures by using monosaccharide backbones with diverse molecular configurations.
Topics: Galactose; Glucose; Monosaccharides; Sugars
PubMed: 34411444
DOI: 10.1002/smll.202102938 -
Biochemical Society Transactions Jun 2020Glycosyltransferases are a large family of enzymes responsible for covalently linking sugar monosaccharides to a variety of organic substrates. These enzymes drive the... (Review)
Review
Glycosyltransferases are a large family of enzymes responsible for covalently linking sugar monosaccharides to a variety of organic substrates. These enzymes drive the synthesis of complex oligosaccharides known as glycans, which play key roles in inter-cellular interactions across all the kingdoms of life; they also catalyze sugar attachment during the synthesis of small-molecule metabolites such as plant flavonoids. A given glycosyltransferase enzyme is typically responsible for attaching a specific donor monosaccharide, via a specific glycosidic linkage, to a specific moiety on the acceptor substrate. However these enzymes are often promiscuous, able catalyze linkages between a variety of donors and acceptors. In this review we discuss distinct classes of glycosyltransferase promiscuity, each illustrated by enzymatic examples from small-molecule or glycan synthesis. We highlight the physical causes of promiscuity, and its biochemical consequences. Structural studies of glycosyltransferases involved in glycan synthesis show that they make specific contacts with 'recognition motifs' that are much smaller than the full oligosaccharide substrate. There is a wide range in the sizes of glycosyltransferase recognition motifs: highly promiscuous enzymes recognize monosaccharide or disaccharide motifs across multiple oligosaccharides, while highly specific enzymes recognize large, complex motifs found on few oligosaccharides. In eukaryotes, the localization of glycosyltransferases within compartments of the Golgi apparatus may play a role in mitigating the glycan variability caused by enzyme promiscuity.
Topics: Amino Acid Motifs; Carbohydrates; Catalysis; Eukaryota; Glycosides; Glycosylation; Glycosyltransferases; Golgi Apparatus; Kinetics; Models, Molecular; Monosaccharides; Oligosaccharides; Polysaccharides; Substrate Specificity
PubMed: 32539082
DOI: 10.1042/BST20190651 -
Methods in Molecular Biology (Clifton,... 2022Glycosaminoglycans (GAGs) are heterogeneous biomacromolecules made by all animal cells with overlapping molecular weight and high negative charge densities, which make...
Glycosaminoglycans (GAGs) are heterogeneous biomacromolecules made by all animal cells with overlapping molecular weight and high negative charge densities, which make thorough separation of different types of GAGs and elimination of all GAG-binding proteins difficult. Even with the constant challenge of quality control, chondroitin sulfate, dermatan sulfate, heparan sulfate, and heparin glycosaminoglycans (GAGs) have been used as nutraceuticals and modern drugs for many years worldwide. Testing galactosamine in heparin has been added to the USP monograph after contaminated heparin event, but the general monosaccharide composition analysis has not been developed for GAG quality control purposes. Using a PCR-facilitated hydrolysis assay, the hydrolyzed GAG saccharides were labeled with 1-phenyl-3-methyl-5-pyrazolone (PMP) and quantified by high performance liquid chromatography (HPLC) coupled with mass spectrometry (MS). Glucosamine was found in both chondroitin sulfate and dermatan sulfate whereas galactosamine was observed in both heparan sulfate and heparin, indicating the cross contamination among different types of GAGs. Moreover, fucose was detected in chondroitin sulfate, dermatan sulfate, and heparan sulfate, and both fucose and mannose were detected in chondroitin sulfate, suggesting the co-presence of other types of glycans or novel fucosylated GAG structures. Furthermore, both the amount and structure of acid-resistant disaccharides provide distinguishable features for each type of GAGs at the same hydrolysis condition. Thus, monosaccharide analysis provides a practical and quantitative way for GAG quality control.
Topics: Animals; Chondroitin Sulfates; Dermatan Sulfate; Fucose; Galactosamine; Glycosaminoglycans; Heparin; Heparitin Sulfate; Monosaccharides; Quality Control
PubMed: 34626388
DOI: 10.1007/978-1-0716-1398-6_24 -
International Journal of Biological... Jun 2023In this study, two homogeneous polysaccharides (APS-A1 and APS-B1) were isolated from Astragalus membranaceus by DEAE-52 cellulose and Sephadex G-100 column...
In this study, two homogeneous polysaccharides (APS-A1 and APS-B1) were isolated from Astragalus membranaceus by DEAE-52 cellulose and Sephadex G-100 column chromatography. Their chemical structures were characterized by molecular weight distribution, monosaccharide composition, infrared spectrum, methylation analysis, and NMR. The results revealed that APS-A1 (2.62 × 10 Da) was a 1,4-α-D-Glcp backbone with a 1,4,6-α-D-Glcp branch every ten residues. APS-B1 (4.95 × 10 Da) was a heteropolysaccharide composed of glucose, galactose, and arabinose (75.24:17.27:19.35). Its backbone consisted of 1,4-α-D-Glcp, 1,4,6-α-D-Glcp, 1,5-α-L-Araf and the sidechains composed of 1,6-α-D-Galp and T-α/β-Glcp. Bioactivity assays showed that APS-A1 and APS-B1 had potential anti-inflammatory activity. They could inhibit the production of inflammatory factors (TNF-α, IL-6, and MCP-1) in LPS-stimulated RAW264.7 macrophages via NF-κB and MAPK (ERK, JNK) pathways. These results suggested that the two polysaccharides could be potential anti-inflammatory supplements.
Topics: Astragalus propinquus; Polysaccharides; Monosaccharides; Macrophages; Anti-Inflammatory Agents
PubMed: 37054858
DOI: 10.1016/j.ijbiomac.2023.124386 -
International Journal of Biological... Jul 2023Fritillaria is a traditional Chinese medicine(TCM) with a history of thousands of years. Fritillaria always contain saponins, alkaloids, amino acids, flavones, and... (Review)
Review
Fritillaria is a traditional Chinese medicine(TCM) with a history of thousands of years. Fritillaria always contain saponins, alkaloids, amino acids, flavones, and polysaccharides. Among them, Fritillaria polysaccharide has a variety of biological activities. Its anti-inflammatory and antiaging activities are new study hotspots. The extraction, purification, quantitative determination, monosaccharide composition, and biological activity of Fritillaria polysaccharides have been examined for several years in an attempt to identify the active components and understand the pharmacological process. In this review, ample original publications related to the distribution, extraction, purification, quantitative determination, monosaccharide composition and biological activities of Fritillaria until 2023 were searched and collected by using various literature databases. Databases included the China National Knowledge Infrastructure, VIP database, Wan Fang database, PubMed, Elsevier, Springer, Science Direct, Google Scholar and Web of Science database, as well as the classic Chinese medical books and PhD and MSc theses. The properties and outcomes of various extractions, purifications, quantitative determination methods, monosaccharide compositions, and biological activities of Fritillaria polysaccharides are discussed here. Additionally, we summarize the research potential of Fritillaria polysaccharide and identify promising research direction candidates.
Topics: Fritillaria; Medicine, Chinese Traditional; Drugs, Chinese Herbal; Monosaccharides; Polysaccharides; Phytochemicals
PubMed: 37182621
DOI: 10.1016/j.ijbiomac.2023.124817 -
Effect of monosaccharide composition and proportion on the bioactivity of polysaccharides: A review.International Journal of Biological... Jan 2024Polysaccharides have been widely used in pharmaceutical and food industries due to their diverse bioactivity, high safety, and few or no side effects. However, inability... (Review)
Review
Polysaccharides have been widely used in pharmaceutical and food industries due to their diverse bioactivity, high safety, and few or no side effects. However, inability to quickly produce, screen, and synthesize bioactive polysaccharides is the limiting factor for their development and application. Structural features determine and influence the bioactivity of polysaccharides. Among them, monosaccharide is the basic unit of polysaccharide, which not only affects electrification, functional group, and bioactivity of polysaccharide but also is one of the simplest polysaccharide indexes to be detected. At present, effects of monosaccharide composition and proportion on anti-inflammatory, antioxidant, antitumor, immunomodulatory, antibacterial, and prebiotic activities of polysaccharides are reviewed. Further problems need to be considered during regulation and analysis of monosaccharide composition and proportion of polysaccharides. Overall, present work will provide help and reference for production, development, and structure-function investigation of polysaccharides based on their monosaccharide.
Topics: Monosaccharides; Polysaccharides; Antioxidants
PubMed: 37944714
DOI: 10.1016/j.ijbiomac.2023.127955 -
Molecules (Basel, Switzerland) Nov 2021Organocatalysis is a very useful tool for the asymmetric synthesis of biologically or pharmacologically active compounds because it avoids the use of noxious metals,... (Review)
Review
Organocatalysis is a very useful tool for the asymmetric synthesis of biologically or pharmacologically active compounds because it avoids the use of noxious metals, which are difficult to eliminate from the target products. Moreover, in many cases, the organocatalysed reactions can be performed in benign solvents and do not require anhydrous conditions. It is well-known that most of the above-mentioned reactions are promoted by a simple aminoacid, l-proline, or, to a lesser extent, by the more complex cinchona alkaloids. However, during the past three decades, other enantiopure natural compounds, the carbohydrates, have been employed as organocatalysts. In the present exhaustive review, the detailed preparation of all the sugar-based organocatalysts as well as their catalytic properties are described.
Topics: Carbohydrates; Catalysis; Epoxy Compounds; Monosaccharides; Oxidation-Reduction; Polysaccharides
PubMed: 34885873
DOI: 10.3390/molecules26237291 -
Biochimica Et Biophysica Acta. General... Dec 2022Fucose (Fuc), a monosaccharide present at the core or the termini of glycans, critically regulates various biological phenomena and is associated with various diseases.... (Review)
Review
BACKGROUND
Fucose (Fuc), a monosaccharide present at the core or the termini of glycans, critically regulates various biological phenomena and is associated with various diseases. Specifically detecting Fuc residues or inhibiting the fucosylation pathway is pivotal in understanding the mechanisms of how fucosylated glycans are related to biological processes and diseases and in developing novel therapeutic agents.
SCOPE OF REVIEW
This review focuses on chemical biology approaches using Fuc analogs developed for metabolically labeling fucosylated glycans or inhibiting the biosynthesis of fucosylated glycans.
MAJOR CONCLUSIONS
Developed Fuc analogs have different potency, specificity and effects on protein and cellular functions. Developing highly enzyme-specific probes and inhibitors is desirable for future investigations.
GENERAL SIGNIFICANCE
Chemical glycobiology approaches using sugar analogs are useful for revealing novel mechanisms of inter-relationships among sugar metabolism pathways and manipulating glycan expression to develop new glycan-targeted therapies.
Topics: Fucose; Monosaccharides; Polysaccharides; Glycosylation
PubMed: 36087787
DOI: 10.1016/j.bbagen.2022.130243 -
Journal of the Science of Food and... Nov 2022Taro, a staple food for residents in Africa and parts of Asia, is an important source of carbohydrate. China has abundant taro resources. Taro contains polysaccharide,... (Review)
Review
Taro, a staple food for residents in Africa and parts of Asia, is an important source of carbohydrate. China has abundant taro resources. Taro contains polysaccharide, vitamins, minerals and other substances. Taro polysaccharides, as a significant active ingredient in taro, are mainly composed of monosaccharide units such as glucose, galactose, arabinose, mannose, and so on. Taro polysaccharides have antioxidant, lipid-lowering, and immunomodulatory effects. In today's world, people are interested in food containing natural ingredients, which stimulates the potential of taro polysaccharides in the food, pharmaceutical, medical, and other fields. Herein, the extraction and purification, structural characterization, functional activity, and application of taro polysaccharides are reviewed to strengthen the cognition of taro polysaccharides. It provides references for further research and development of taro polysaccharides. © 2022 Society of Chemical Industry.
Topics: Antioxidants; Arabinose; Colocasia; Galactose; Glucose; Humans; Lipids; Mannose; Monosaccharides; Pharmaceutical Preparations; Polysaccharides; Vitamins
PubMed: 35679352
DOI: 10.1002/jsfa.12058