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D-Glucuronic acid Sale

(Synonyms: D-葡萄糖醛酸) 目录号 : GC38249

A metabolite of glucose

D-Glucuronic acid Chemical Structure

Cas No.:6556-12-3

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产品描述

D-Glucuronic acid is a metabolite of glucose.1,2 It is formed from glucose in a multi-step process in which uridine diphosphate glucose is dehydrogenated to uridine diphosphate glucuronic acid , from which D-glucuronic acid can be transferred to a receptor to form glucuronides, further metabolized to ascorbic acid or xylulose, or excreted.1 D-Glucuronic acid is a component of proteoglycans, including heparan sulfate and chondroitin sulfate.3 Levels of D-glucuronic acid are increased in fibroblasts isolated from patients with infantile free sialic acid storage disease (ISSD) or Salla disease, lysosomal storage disorders characterized by truncal ataxia and psychomotor retardation and heptatosplenomegaly and impaired growth, respectively.4

1.Miettinen, T.A., and Leskinen, E.Enzyme levels of glucuronic acid metabolism in the liver, kidney and intestine of normal and fasted ratsBiochem. Pharmacol.12(6)565-575(1963) 2.Dutton, G.J., and Storey, I.D.E.Glucuronide-forming enzymes: UDPglucuronic acid + R·OH → UDP + R·O· glucuronic acidMethods in Enzymology5159-164(1962) 3.Kwok, J.C.F., Warren, P., and Fawcett, J.W.Chondroitin sulfate: A key molecule in the brain matrixInt. J. Biochem. Cell Biol.44(4)582-586(2012) 4.Blom, H.J., Andersson, H.C., Seppala, R., et al.Defective glucuronic acid transport from lysosomes of infantile free sialic acid storage disease fibroblastsBiochem. J.268(3)621-625(1990)

Chemical Properties

Cas No. 6556-12-3 SDF
别名 D-葡萄糖醛酸
Canonical SMILES O=C[C@@H]([C@H]([C@@H]([C@@H](C(O)=O)O)O)O)O
分子式 C6H10O7 分子量 194.14
溶解度 DMSO: slightly soluble,PBS (pH 7.2): 10 mg/ml 储存条件 Store at -20°C
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1 mM 5.1509 mL 25.7546 mL 51.5092 mL
5 mM 1.0302 mL 5.1509 mL 10.3018 mL
10 mM 0.5151 mL 2.5755 mL 5.1509 mL
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Research Update

Advantages of Hyaluronic Acid and Its Combination with Other Bioactive Ingredients in Cosmeceuticals

Molecules 2021 Jul 22;26(15):4429.PMID:34361586DOI:10.3390/molecules26154429.

This study proposes a review on hyaluronic acid (HA) known as hyaluronan or hyaluronate and its derivates and their application in cosmetic formulations. HA is a glycosaminoglycan constituted from two disaccharides (N-acetylglucosamine and D-Glucuronic acid), isolated initially from the vitreous humour of the eye, and subsequently discovered in different tissues or fluids (especially in the articular cartilage and the synovial fluid). It is ubiquitous in vertebrates, including humans, and it is involved in diverse biological processes, such as cell differentiation, embryological development, inflammation, wound healing, etc. HA has many qualities that recommend it over other substances used in skin regeneration, with moisturizing and anti-ageing effects. HA molecular weight influences its penetration into the skin and its biological activity. Considering that, nowadays, hyaluronic acid has a wide use and a multitude of applications (in ophthalmology, arthrology, pneumology, rhinology, aesthetic medicine, oncology, nutrition, and cosmetics), the present study describes the main aspects related to its use in cosmetology. The biological effect of HA on the skin level and its potential adverse effects are discussed. Some available cosmetic products containing HA have been identified from the brand portfolio of most known manufacturers and their composition was evaluated. Further, additional biological effects due to the other active ingredients (plant extracts, vitamins, amino acids, peptides, proteins, saccharides, probiotics, etc.) are presented, as well as a description of their possible toxic effects.

D-Glucuronic Acid-Coated Ultrasmall Bi₂O₃ Nanoparticles for CT Imaging

J Nanosci Nanotechnol 2020 Aug 1;20(8):4638-4642.PMID:32126632DOI:10.1166/jnn.2020.17817.

Ultrasmall Bi₂O₃ nanoparticles (davg = 1.5 nm) coated with biocompatible and hydrophilic D-Glucuronic acid were prepared for the first time through a simple one-step polyol process and their potential as CT contrast agents were investigated by measuring their X-ray attenuation properties. Their observed X-ray attenuation power was stronger than that of a commercial iodine CT contrast agent at the same atomic concentration, as consistent with the magnitudes of atomic X-ray attenuation coefficients (i.e., Bi > I), and much stronger at the same number density. The results indicate that the nanoparticle sample is a potential CT contrast agent.

Global transcriptional profiling of tyramine and D-Glucuronic acid catabolism in Salmonella

Int J Med Microbiol 2020 Dec;310(8):151452.PMID:33091748DOI:10.1016/j.ijmm.2020.151452.

Salmonella has evolved various metabolic pathways to scavenge energy from the metabolic byproducts of the host gut microbiota, however, the precise metabolic byproducts and pathways utilized by Salmonella remain elusive. Previously we reported that Salmonella can proliferate by deriving energy from two metabolites that naturally occur in the host as gut microbial metabolic byproducts, namely, tyramine (TYR, an aromatic amine) and D-Glucuronic acid (DGA, a hexuronic acid). Salmonella Pathogenicity Island 13 (SPI-13) plays a critical role in the ability of Salmonella to derive energy from TYR and DGA, however the catabolic pathways of these two micronutrients in Salmonella are poorly defined. The objective of this study was to identify the specific genetic components and construct the regulatory circuits for the TYR and DGA catabolic pathways in Salmonella. To accomplish this, we employed TYR and DGA-induced global transcriptional profiling and gene functional network analysis approaches. We report that TYR induced differential expression of 319 genes (172 up-regulated and 157 down-regulated) when Salmonella was grown in the presence of TYR as a sole energy source. These included the genes originally predicted to be involved in the classical TYR catabolic pathway. TYR also induced expression of majority of genes involved in the acetaldehyde degradation pathway and aided identification of a few new genes that are likely involved in alternative pathway for TYR catabolism. In contrast, DGA induced differential expression of 71 genes (58 up-regulated and 13 down-regulated) when Salmonella was grown in the presence of DGA as a sole energy source. These included the genes originally predicted to be involved in the classical pathway and a few new genes likely involved in the alternative pathway for DGA catabolism. Interestingly, DGA also induced expression of SPI-2 T3SS, suggesting that DGA may also influence nutritional virulence of Salmonella. In summary, this is the first report describing the global transcriptional profiling of TYR and DGA catabolic pathways of Salmonella. This study will contribute to the better understanding of the role of TYR and DGA in metabolic adaptation and virulence of Salmonella.

In Situ Synthesis of Silver Nanoparticles on Cellulose Fibers Using D-Glucuronic acid and Its Antibacterial Application

Materials (Basel) 2019 Sep 23;12(19):3101.PMID:31547568DOI:10.3390/ma12193101.

The development of ecofriendly procedures to avoid the use of toxic chemicals for the synthesis of stable silver nanoparticles (AgNPs) is highly desired. In the present study, we reported an eco-friendly and green technique for in situ fabrication of AgNPs on bleached hardwood pulp fibers (bhpFibers) using D-Glucuronic acid as the only reducing agent. Different amounts of D-Glucuronic acid were introduced and its effect on the size and distribution of AgNPs on the bhpFibers was discussed. The morphology and structures of bhpFibers@AgNPs were proved by electron microscope-dispersive spectroscopy (SEM-EDS), X-ray diffraction (XRD), Fourier transform infrared (FT-IR) and X-ray photoelectron spectroscopy (XPS). Then, a series of bhpFibers@AgNPs with different AgNPs loadings were also prepared by adjusting the concentration of the AgNO3 solution. After a papermaking process via vacuum filtration, the prepared papers displayed an outstanding antibacterial performance against Escherichia coli (gram -negative) and Staphylococcus aureus (gram-positive). It is foreseeable that the bhpFibers@AgNPs have a promising application in the field of biomedical.

Phenelzine and Amoxapine Inhibit Tyramine and D-Glucuronic acid Catabolism in Clinically Significant Salmonella in A Serotype-Independent Manner

Pathogens 2021 Apr 13;10(4):469.PMID:33924374DOI:10.3390/pathogens10040469.

Non-typhoidal Salmonella ingeniously scavenges energy for growth from tyramine (TYR) and D-Glucuronic acid (DGA), both of which occur in the host as the metabolic byproducts of the gut microbial metabolism. A critical first step in energy scavenging from TYR and DGA in Salmonella involves TYR-oxidation via TYR-oxidoreductase and production of free-DGA via β-glucuronidase (GUS)-mediated hydrolysis of d-glucuronides (conjugated form of DGA), respectively. Here, we report that Salmonella utilizes TYR and DGA as sole sources of energy in a serotype-independent manner. Using colorimetric and radiometric approaches, we report that genes SEN2971, SEN3065, and SEN2426 encode TYR-oxidoreductases. Some Salmonella serotypes produce GUS, thus can also scavenge energy from d-glucuronides. We repurposed phenelzine (monoaminoxidase-inhibitor) and amoxapine (GUS-inhibitor) to inhibit the TYR-oxidoreductases and GUS encoded by Salmonella, respectively. We show that phenelzine significantly inhibits the growth of Salmonella by inhibiting TYR-oxidoreductases SEN2971, SEN3065, and SEN2426. Similarly, amoxapine significantly inhibits the growth of Salmonella by inhibiting GUS-mediated hydrolysis of d-glucuronides. Because TYR and DGA serve as potential energy sources for Salmonella growth in vivo, the data and the novel approaches used here provides a better understanding of the role of TYR and DGA in Salmonella pathogenesis and nutritional virulence.