7512-17-6 Usage
Description
N-Acetyl-D-Glucosamine is the N-acetyl derivative of glucosamine.Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc regulates cellular responses to hormones such as insulin, initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. In humans, it exists in skin, cartilage and blood vessel as a component of hyaluronic acid, and bone tissue, cornea and aorta as a component of keratan sulfate.
N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. It is also synthesized in the glycosylation pathway as uridine diphosphate (UDP-GlcNAc), which can then be released following degradation of glycosylated proteins.D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s). It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.
Chemical Properties
White powder
Uses
Different sources of media describe the Uses of 7512-17-6 differently. You can refer to the following data:
1. A pharmaceutical and cosmetic compound.
2. N-acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose. It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc. Levels of O-GlcNAcylation proteins from Alzheimer’s disease brain extracts are decreased as compared to that in controls, suggesting that release of GlcNAc may contribute to pathogenesis.1 In E. coli, GlcNAc induces the expression of multidrug exporter genes, indicating that this sugar can alter gene expression.1 GlcNAc is also the monomeric unit of chitin, which is found in fungi and many invertebrates, including crustaceans, insects, and nematodes. For this reason, chemicals that inhibit the incorporation of GlcNAc into chitin are cytotoxic to these organisms.
Atypical microbial danger signal that acts as a new activator of NLRP3 inflammasome by dissociating the enzyme hexokinase from the mitochondria. D-GlcNAc inhibits purified hexokinase, which is also involved in the glucose metabolism and obesity in mM range. For hexokinase dissociation from the mitochondria much higher concentrations are needed.
Acceptor substrate for galactosyltransferases. Inhibits the lectin WGA and is used to identify, differentiate and characterize N-acetyl-β-D-hexosaminidase(s).
Used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Significantly enhances the prevention of joint damage and inhibits elastase activity and superoxide release from human polymorphonuclear leukocytes. Acts as a cytoprotective agent restoring the integrity and normal function of mucous membrane in humans.
D-GlcNAc enhances the proliferation and collagen expression of fibroblasts, reduces hyperpigmentation and is therefore considered a valuable ingredient in cosmetics for improving skin wrinkles and color.
Important substrate for the production of sialic acids.
Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.
3. N-Acetyl-D-glucosamine is used in the identification and characterization of N-acetyl-beta-D-hexoaminidase. It is also used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Further, it is used as a substrate in sialic acid production, cosmetics and in drug development research.
Definition
ChEBI: The pyranose form of N-acetyl-D-glucosamine.
General Description
N-Acetylglucosamine (GlcNAc) is a monosaccharide, derived from glucose and undergoes linear polymerization by (1,4)-β-linkages to form the polymer chitin. It is also a component of heterogenous polysaccharides, such as murein and hyaluronic acid. N-acetylglucosamine exhibits anti-inflammatory properties and is considered as a potential drug in the treatment of osteoarthritis. Its antiarthritic mode of mechanism involves the suppression of IL-1β (Interleuken-1β)-induced NO (nitric oxide), cyclooxygenase-2 (COX-2), and IL-6 production by inhibition of expression of iNOS (inducible nitric oxide synthase) protein and mRNA.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
N-Acetylglucosamine (GlcNAc) oligomer may have the ability to initiate factors for canine polymorphonuclear cells (PMN) in vivo. It possesses wound healing and chemotactic activity. GlcNAc and its derivatives are usually employed in preparing dietary supplements and also used in therapeutic development.
Check Digit Verification of cas no
The CAS Registry Mumber 7512-17-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,1 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 7512-17:
(6*7)+(5*5)+(4*1)+(3*2)+(2*1)+(1*7)=86
86 % 10 = 6
So 7512-17-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)
7512-17-6Relevant articles and documents
Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian
, p. 359 - 364 (2020/12/28)
Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives
Cao, Zhi-Ling,Liu, Shu-Hao,Liu, Wei-Wei,Ren, Shu-Ting,Shi, Da-Hua,Wang, Lei,Wang, You-Xian,Wu, Yu-Ran
, p. 363 - 366 (2020/02/05)
Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.
Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.
, p. 2367 - 2380 (2020/08/28)
Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.
