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132489-69-1,MFCD00145022
Catalog No.:AA0010NN

132489-69-1 | O-(2-Acetamido-2-deoxy-d-glucopyranosylidene)amino n-phenyl carbamate

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1mg
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5mg
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10mg
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA0010NN
Chemical Name:
O-(2-Acetamido-2-deoxy-d-glucopyranosylidene)amino n-phenyl carbamate
CAS Number:
132489-69-1
Molecular Formula:
C15H19N3O7
Molecular Weight:
353.3273
MDL Number:
MFCD00145022
SMILES:
OCC1OC(=NOC(=O)Nc2ccccc2)C(C(C1O)O)NC(=O)C
Properties
Computed Properties
 
Complexity:
507  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
5  
XLogP3:
-0.3  

Literature

Title: Hyper-O-GlcNAcylation inhibits the induction of heat shock protein 70 (Hsp 70) by sodium arsenite in HeLa cells.

Journal: Biological & pharmaceutical bulletin 20140101

Title: Computational analysis of human OGA structure in complex with PUGNAc and NAG-thiazoline derivatives.

Journal: Journal of chemical information and modeling 20121022

Title: Evidence of the involvement of O-GlcNAc-modified human RNA polymerase II CTD in transcription in vitro and in vivo.

Journal: The Journal of biological chemistry 20120706

Title: Beta-hexosaminidase activity of the oral pathogen Tannerella forsythia influences biofilm formation on glycoprotein substrates.

Journal: FEMS immunology and medical microbiology 20120601

Title: Glucosamine modulates TNF-α-induced ICAM-1 expression and function through O-linked and N-linked glycosylation in human retinal pigment epithelial cells.

Journal: Investigative ophthalmology & visual science 20120424

Title: PUGNAc treatment leads to an unusual accumulation of free oligosaccharides in CHO cells.

Journal: Journal of biochemistry 20120401

Title: Identification of a specific inhibitor of nOGA - a caspase-3 cleaved O-GlcNAcase variant during apoptosis.

Journal: Biochemistry. Biokhimiia 20120201

Title: Modulators of sensitivity and resistance to inhibition of PI3K identified in a pharmacogenomic screen of the NCI-60 human tumor cell line collection.

Journal: PloS one 20120101

Title: Active-pocket size differentiating insectile from bacterial chitinolytic β-N-acetyl-D-hexosaminidases.

Journal: The Biochemical journal 20110915

Title: Down-regulation of β-N-acetyl-D-glucosaminidase increases Akt1 activity in thyroid anaplastic cancer cells.

Journal: Oncology reports 20110901

Title: O-GlcNAcylation increases non-amyloidogenic processing of the amyloid-β precursor protein (APP).

Journal: Biochemical and biophysical research communications 20110121

Title: O-GlcNAc modification of NFκB p65 inhibits TNF-α-induced inflammatory mediator expression in rat aortic smooth muscle cells.

Journal: PloS one 20110101

Title: The role of O-linked GlcNAc modification on the glucose response of ChREBP.

Journal: Biochemical and biophysical research communications 20101126

Title: Inhibition of phospholamban phosphorylation by O-GlcNAcylation: implications for diabetic cardiomyopathy.

Journal: Glycobiology 20101001

Title: Inhibition of O-GlcNAcase using a potent and cell-permeable inhibitor does not induce insulin resistance in 3T3-L1 adipocytes.

Journal: Chemistry & biology 20100924

Title: Quantification of O-glycosylation stoichiometry and dynamics using resolvable mass tags.

Journal: Nature chemical biology 20100901

Title: Cytoskeletal keratin glycosylation protects epithelial tissue from injury.

Journal: Nature cell biology 20100901

Title: Stressing the role of O-GlcNAc: linking cell survival to keratin modification.

Journal: Nature cell biology 20100901

Title: O-GlcNAc modification of proteins affects volume regulation in Jurkat cells.

Journal: European biophysics journal : EBJ 20100701

Title: An improved route to PUGNAc and its galacto-configured congener.

Journal: The Journal of organic chemistry 20100604

Title: Quantum mechanical/molecular mechanical molecular dynamics simulation of wild-type and seven mutants of CpNagJ in complex with PUGNAc.

Journal: The journal of physical chemistry. B 20100527

Title: Development of GlcNAc-inspired iminocyclitiols as potent and selective N-acetyl-beta-hexosaminidase inhibitors.

Journal: ACS chemical biology 20100521

Title: Glycopeptide-specific monoclonal antibodies suggest new roles for O-GlcNAc.

Journal: Nature chemical biology 20100501

Title: Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase.

Journal: Biochimica et biophysica acta 20100201

Title: O-linked beta-N-acetylglucosaminylation in mouse embryonic neural precursor cells.

Journal: Journal of neuroscience research 20091201

Title: O-GlcNAc signaling attenuates ER stress-induced cardiomyocyte death.

Journal: American journal of physiology. Heart and circulatory physiology 20091101

Title: Excessive O-GlcNAcylation of proteins suppresses spontaneous cardiogenesis in ES cells.

Journal: FEBS letters 20090806

Title: Insight into a strategy for attenuating AmpC-mediated beta-lactam resistance: structural basis for selective inhibition of the glycoside hydrolase NagZ.

Journal: Protein science : a publication of the Protein Society 20090701

Title: O-GLcNAc post-translational modifications regulate the entry of neurons into an axon branching program.

Journal: Developmental neurobiology 20090201

Title: Unique hexosaminidase reduces metabolic survival signal and sensitizes cardiac myocytes to hypoxia/reoxygenation injury.

Journal: Circulation research 20090102

Title: O-linked beta-N-acetylglucosamine: a new piece of the cardioprotection puzzle?

Journal: Circulation research 20090102

Title: Elevation of global O-GlcNAc levels in 3T3-L1 adipocytes by selective inhibition of O-GlcNAcase does not induce insulin resistance.

Journal: The Journal of biological chemistry 20081212

Title: A quantum mechanics/molecular mechanics study of the protein-ligand interaction of two potent inhibitors of human O-GlcNAcase: PUGNAc and NAG-thiazoline.

Journal: The journal of physical chemistry. B 20081113

Title: The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc.

Journal: Carbohydrate research 20081103

Title: Increased protein O-GlcNAc modification inhibits inflammatory and neointimal responses to acute endoluminal arterial injury.

Journal: American journal of physiology. Heart and circulatory physiology 20080701

Title: O-glycosylation of FoxO1 increases its transcriptional activity towards the glucose 6-phosphatase gene.

Journal: FEBS letters 20080305

Title: Proteomic analysis of O-GlcNAc modifications derived from streptozotocin and glucosamine induced beta-cell apoptosis.

Journal: Journal of biochemistry and molecular biology 20071130

Title: O-GlcNAc modification modulates the expression of osteocalcin via OSE2 and Runx2.

Journal: Biochemical and biophysical research communications 20071019

Title: Increased O-GlcNAc levels during reperfusion lead to improved functional recovery and reduced calpain proteolysis.

Journal: American journal of physiology. Heart and circulatory physiology 20070901

Title: The sweet nature of cardioprotection.

Journal: American journal of physiology. Heart and circulatory physiology 20070901

Title: Small molecule inhibitors of a glycoside hydrolase attenuate inducible AmpC-mediated beta-lactam resistance.

Journal: The Journal of biological chemistry 20070720

Title: Glucosamine-induced increase in Akt phosphorylation corresponds to increased endoplasmic reticulum stress in astroglial cells.

Journal: Molecular and cellular biochemistry 20070401

Title: The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels.

Journal: Shock (Augusta, Ga.) 20070401

Title: Analysis of PUGNAc and NAG-thiazoline as transition state analogues for human O-GlcNAcase: mechanistic and structural insights into inhibitor selectivity and transition state poise.

Journal: Journal of the American Chemical Society 20070124

Title: Inhibition of O-GlcNAcase by a gluco-configured nagstatin and a PUGNAc-imidazole hybrid inhibitor.

Journal: Chemical communications (Cambridge, England) 20061113

Title: Akt1 is dynamically modified with O-GlcNAc following treatments with PUGNAc and insulin-like growth factor-1.

Journal: FEBS letters 20060529

Title: Structural insights into the mechanism and inhibition of eukaryotic O-GlcNAc hydrolysis.

Journal: The EMBO journal 20060405

Title: An O-GlcNAcase-specific inhibitor and substrate engineered by the extension of the N-acetyl moiety.

Journal: Journal of the American Chemical Society 20060405

Title: A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase.

Journal: Organic & biomolecular chemistry 20060307

Title: Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry.

Journal: Bioorganic & medicinal chemistry 20060201

Title: O-GlcNAc modification on IRS-1 and Akt2 by PUGNAc inhibits their phosphorylation and induces insulin resistance in rat primary adipocytes.

Journal: Experimental & molecular medicine 20050630

Title: Protein O-GlcNAc modulates motility-associated signaling intermediates in neutrophils.

Journal: The Journal of biological chemistry 20050415

Title: Selective decrease of membrane-associated PKC-alpha and PKC-epsilon in response to elevated intracellular O-GlcNAc levels in transformed human glial cells.

Journal: Biochimica et biophysica acta 20050415

Title: Relationship between protein O-linked glycosylation and insulin-stimulated glucose transport in rat skeletal muscle following calorie restriction or exposure to O-(2-acetamido-2-deoxy-d-glucopyranosylidene)amino-N-phenylcarbamate.

Journal: Acta physiologica Scandinavica 20050301

Title: Prolonged incubation in PUGNAc results in increased protein O-Linked glycosylation and insulin resistance in rat skeletal muscle.

Journal: Diabetes 20040401

Title: Cytosolic O-GlcNAc accumulation is not involved in beta-cell death in HIT-T15 or Min6.

Journal: Biochemical and biophysical research communications 20010921

Title: O-GlcNAc expression in developing and ageing mouse brain.

Journal: Biochimie 20010701

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Tags:132489-69-1 Molecular Formula|132489-69-1 MDL|132489-69-1 SMILES|132489-69-1 O-(2-Acetamido-2-deoxy-d-glucopyranosylidene)amino n-phenyl carbamate