Synthesis of Lipid-Linked Oligosaccharides (LLOs) and Their Phosphonate Analogues as Probes To Study Protein Glycosylation Enzymes

Synthesis ◽  
2018 ◽  
Vol 50 (14) ◽  
pp. 2631-2654 ◽  
Author(s):  
Jean-Louis Reymond ◽  
Jérémy Boilevin

Here we review chemical and chemoenzymatic methods for the synthesis of lipid-linked oligosaccharides (LLOs) and their phosphonate analogues, which serve as substrates and inhibitors to investigate the structure and mechanism of protein N-glycosylation enzymes. We emphasize how to overcome the challenges pertaining to the instability and difficult physicochemical properties of this class of compounds.1 Introduction2 LLO Syntheses2.1 Glycosyl Phosphate Syntheses2.2 Glycosyl Phosphonates2.3 Lipid Elongation2.4 Lipid Phosphates2.5 Coupling Reaction Strategies3 Chemoenzymatic Synthesis of Elongated LLOs4 Biological Properties of Synthetic LLOs5 Conclusion

2021 ◽  
Vol 47 (1) ◽  
pp. 1244-1252
Author(s):  
Liguo Zhang ◽  
Can Zhang ◽  
Enxia Xu ◽  
Lu Gao ◽  
Huiping Chen ◽  
...  

Materials ◽  
2020 ◽  
Vol 13 (14) ◽  
pp. 3224 ◽  
Author(s):  
Beata Kaczmarek

As a phenolic acid, tannic acid can be classified into a polyphenolic group. It has been widely studied in the biomedical field of science because it presents unique antiviral as well as antibacterial properties. Tannic acid has been reported to present the activity against Influeneza A virus, Papilloma viruses, noroviruses, Herpes simplex virus type 1 and 2, and human immunodeficiency virus (HIV) as well as activity against both Gram-positive and Gram-negative bacteria as Staphylococcus aureus, Escherichia coli, Streptococcus pyogenes, Enterococcus faecalis, Pseudomonas aeruginosa, Yersinia enterocolitica, Listeria innocua. Nowadays, compounds of natural origin constitute fundaments of material science, and the trend is called “from nature to nature”. Although biopolymers have found a broad range of applications in biomedical sciences, they do not present anti-microbial activity, and their physicochemical properties are rather poor. Biopolymers, however, may be modified with organic and inorganic additives which enhance their properties. Tannic acid, like phenolic acid, is classified into a polyphenolic group and can be isolated from natural sources, e.g., a pure compound or a component of a plant extract. Numerous studies have been carried out over the application of tannic acid as an additive to biopolymer materials due to its unique properties. On the one hand, it shows antimicrobial and antiviral activity, while on the other hand, it reveals promising biological properties, i.e., enhances the cell proliferation, tissue regeneration and wound healing processes. Tannic acid is added to different biopolymers, collagen and polysaccharides as chitosan, agarose and starch. Its activity has been proven by the determination of physicochemical properties, as well as the performance of in vitro and in vivo studies. This systematics review is a summary of current studies on tannic acid properties. It presents tannic acid as an excellent natural compound which can be used to eliminate pathogenic factors as well as a revision of current studies on tannic acid composed with biopolymers and active properties of the resulting complexes.


1976 ◽  
Vol 159 (3) ◽  
pp. 661-665 ◽  
Author(s):  
F Gauthier ◽  
H Mouray

1. Rat α2 acute-phase macroglobulin was isolated from turpentine-injected rats by Sephadex G-200 chromatography and ion-exchange chromatography on DEAE-cellulose. This method, since it does not include (NH4)2SO4 treatment, allows the study of the physicochemical as well as the biological properties of the molecule. 2. The purity of the preparation was demonstrated by ultracentrifugation, polyacrylamide-gel electrophoresis, fused “rocket” immunoelectrophoresis as well as double immunodiffusion. 3. The rat α2 acute-phase macroglobulin was characterized in terms of its main physical and chemical properties. Its isoelctric point was determined by isoelectrofocusing to be 4.55; s020,w was 18.4S and E1%/1cm at 278 nm was 6.8. The mol.wt. was determined by light-scattering to be 770000. 4. The amino acid content was compared with that of rat α1 macroglobulin and was found very similar. The carbohydrate composition of α2 acute-phase macroglobulin was determined to be: hexose, 4.25%; glucosamine, 3.4%; sialic acid, 2%; fucose, 0.2%. From these results it was concluded that α2 acute-phase macroglobulin, although a typical acute-phase reactant, possesses the characteristic physicochemical properties of α macroglobulins.


2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Danilo Aleo ◽  
Venera Cardile ◽  
Rosa Chillemi ◽  
Giuseppe Granata ◽  
Sebastiano Sciuto

3- O-, 3,5-di- O- and 4′- O-phosphoryl derivatives of ( E)-resveratrol have been obtained following a chemoenzymatic strategy. Variedly acylated resveratrol derivatives have been obtained first by exploiting regioselective properties of Pseudomonas cepacea or Candida antarctica lipases in organic solvents. Each acyl-resveratrol was then phosphorylated by the phosphoramidite chemistry protocol and in sequence freed of protective groups, affording the desired O-phosphoryl derivative. Following UV-absorption spectroscopic investigation on the interaction of the newly synthesized compounds with DNA, 4′- O-phosphorylresveratrol exhibited the best binding affinity. As a result of cytotoxicity tests, 3- O-phosphorylresveratrol was more active than resveratrol against DU 145 prostate cancer cells.


2020 ◽  
Vol 26 (36) ◽  
pp. 4648-4657
Author(s):  
Patricia Rocha de Araújo ◽  
Bruno Fonseca-Santos ◽  
Ana Carolina Kogawa ◽  
Hérida Regina Nunes Salgado ◽  
Marlus Chorilli

Aims: A review of analytical methods for the determination of hypericin in foods, herbal, biological and pharmaceutical matrices. Background: Hypericin (HYP) is a naturally-occurring pigment obtained from some plants of the genus Hypericum. Although HYP has been known for many years, it has recently attracted attention due to its varied biological properties, such as anti-inflammatory and antidepressant activity and it is also an efficient photosensitizer. Objective: The objective of this review is to provide insights into the physicochemical properties of HYP, as well as to report the analytical methods existing in the literature and official compendia for different matrices. Methods: The survey data were collected by Google Scholar® and Scopus® using keys terms. Result: Analytical methods involving HYP are mainly concerned with the quality control of pharmaceutical preparations, foods, beverages, biological samples and drug delivery systems using different types of analysis methods. Some difficulties have also been identified due to the physicochemical properties of HYP. It presents great solubility in alkaline solutions, organic bases and common polar organic solvents. Conclusion: It can be analyzed by thin layer chromatography, spectrophotometry in the ultraviolet region, but the most commonly used method is by HPLC. HYP presents monographs in the American, British and European Pharmacopoeias, however, the methods of analysis are not yet harmonized.


2010 ◽  
Vol 14 (02) ◽  
pp. 150-157 ◽  
Author(s):  
Hai-Ying Zhan ◽  
Hai-Yang Liu ◽  
Jun Lu ◽  
A-Zhong Wang ◽  
Li-Li You ◽  
...  

Alkynyl corroles were synthesized from iodidphenyl corrole precursor by using Sonogashira coupling reaction with or without the presence of copper(I) iodide co-catalyst. The alkynyl group on corrole macrocycle has a significant effect on the photophysical and electrochemical properties of free-base and metal corrole derivatives.


2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
A. Nasiru ◽  
N. Ismail ◽  
M. H. Ibrahim

Ruminants are important sources of meat and milk. Their production is associated with manure excretion. Estimates of over 3,900,000 million metric tonnes of manure are produced daily from ruminants worldwide. Storage and spread of this waste on land pose health risks and environmental problems. Efficient and sustainable way of handling ruminant manure is required. Composting and vermicomposting are considered two of the best techniques for solid biomass waste management. This paper presents vermicomposting as an effective tool for ruminant manure management. Vermicomposting is a mesophilic biooxidation and stabilisation process of organic materials that involves the joint action of earthworm and microorganism. Compared with composting, vermicomposting has higher rate of stabilisation and it is greatly modifying its physical and biochemical properties, with low C : N ratio and homogenous end product. It is also costeffective and ecofriendly waste management. Due to its innate biological, biochemical and physicochemical properties, vermicomposting can be used to promote sustainable ruminant manure management. Vermicomposts are excellent sources of biofertiliser and their addition improves the physiochemical and biological properties of agricultural soils. In addition, earthworms from the vermicomposting can be used as source of protein to fishes and monogastric animals. Vermicompost can also be used as raw materials for bioindustries.


2013 ◽  
Vol 15 (14) ◽  
pp. 3558-3561 ◽  
Author(s):  
Ning-hui Chang ◽  
Xi-chao Chen ◽  
Hikaru Nonobe ◽  
Yasuhiro Okuda ◽  
Hiroki Mori ◽  
...  

RSC Advances ◽  
2015 ◽  
Vol 5 (19) ◽  
pp. 14294-14304 ◽  
Author(s):  
Loredana S. Dorobantu ◽  
Greg G. Goss ◽  
Robert E. Burrell

The purpose of this study was to characterize the interactive effects of light and aging on physicochemical properties and antimicrobial activity of nanocrystalline silver wound dressings Acticoat that might find their way into the environment.


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