Home Aminos O-(2-Acetamido-2-deoxy-d-glucopyranosylidene)amino n-phenyl carbamate

O-(2-Acetamido-2-deoxy-d-glucopyranosylidene)amino n-phenyl carbamate

CAS No.:
132489-69-1
Catalog Number:
AG0010QF
Molecular Formula:
C15H19N3O7
Molecular Weight:
353.3273
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$91
- +
5mg
≥95%
1 week
United States
$214
- +
10mg
≥95%
1 week
United States
$300
- +
Product Description
Catalog Number:
AG0010QF
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
IUPAC Name:
[(Z)-[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-phenylcarbamate
InChI:
InChI=1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1
InChI Key:
PBLNJFVQMUMOJY-JXZOILRNSA-N
SMILES:
OCC1OC(=NOC(=O)Nc2ccccc2)C(C(C1O)O)NC(=O)C
Properties
Complexity:
507  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
1  
Exact Mass:
353.122g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
353.331g/mol
Monoisotopic Mass:
353.122g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
150A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  
Literature
Title Journal
Hyper-O-GlcNAcylation inhibits the induction of heat shock protein 70 (Hsp 70) by sodium arsenite in HeLa cells. Biological & pharmaceutical bulletin 20140101
Computational analysis of human OGA structure in complex with PUGNAc and NAG-thiazoline derivatives. Journal of chemical information and modeling 20121022
Evidence of the involvement of O-GlcNAc-modified human RNA polymerase II CTD in transcription in vitro and in vivo. The Journal of biological chemistry 20120706
Beta-hexosaminidase activity of the oral pathogen Tannerella forsythia influences biofilm formation on glycoprotein substrates. FEMS immunology and medical microbiology 20120601
Glucosamine modulates TNF-α-induced ICAM-1 expression and function through O-linked and N-linked glycosylation in human retinal pigment epithelial cells. Investigative ophthalmology & visual science 20120424
PUGNAc treatment leads to an unusual accumulation of free oligosaccharides in CHO cells. Journal of biochemistry 20120401
Identification of a specific inhibitor of nOGA - a caspase-3 cleaved O-GlcNAcase variant during apoptosis. Biochemistry. Biokhimiia 20120201
Modulators of sensitivity and resistance to inhibition of PI3K identified in a pharmacogenomic screen of the NCI-60 human tumor cell line collection. PloS one 20120101
Active-pocket size differentiating insectile from bacterial chitinolytic β-N-acetyl-D-hexosaminidases. The Biochemical journal 20110915
Down-regulation of β-N-acetyl-D-glucosaminidase increases Akt1 activity in thyroid anaplastic cancer cells. Oncology reports 20110901
O-GlcNAcylation increases non-amyloidogenic processing of the amyloid-β precursor protein (APP). Biochemical and biophysical research communications 20110121
O-GlcNAc modification of NFκB p65 inhibits TNF-α-induced inflammatory mediator expression in rat aortic smooth muscle cells. PloS one 20110101
The role of O-linked GlcNAc modification on the glucose response of ChREBP. Biochemical and biophysical research communications 20101126
Inhibition of phospholamban phosphorylation by O-GlcNAcylation: implications for diabetic cardiomyopathy. Glycobiology 20101001
Inhibition of O-GlcNAcase using a potent and cell-permeable inhibitor does not induce insulin resistance in 3T3-L1 adipocytes. Chemistry & biology 20100924
Quantification of O-glycosylation stoichiometry and dynamics using resolvable mass tags. Nature chemical biology 20100901
Cytoskeletal keratin glycosylation protects epithelial tissue from injury. Nature cell biology 20100901
Stressing the role of O-GlcNAc: linking cell survival to keratin modification. Nature cell biology 20100901
O-GlcNAc modification of proteins affects volume regulation in Jurkat cells. European biophysics journal : EBJ 20100701
An improved route to PUGNAc and its galacto-configured congener. The Journal of organic chemistry 20100604
Quantum mechanical/molecular mechanical molecular dynamics simulation of wild-type and seven mutants of CpNagJ in complex with PUGNAc. The journal of physical chemistry. B 20100527
Development of GlcNAc-inspired iminocyclitiols as potent and selective N-acetyl-beta-hexosaminidase inhibitors. ACS chemical biology 20100521
Glycopeptide-specific monoclonal antibodies suggest new roles for O-GlcNAc. Nature chemical biology 20100501
Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase. Biochimica et biophysica acta 20100201
O-linked beta-N-acetylglucosaminylation in mouse embryonic neural precursor cells. Journal of neuroscience research 20091201
O-GlcNAc signaling attenuates ER stress-induced cardiomyocyte death. American journal of physiology. Heart and circulatory physiology 20091101
Excessive O-GlcNAcylation of proteins suppresses spontaneous cardiogenesis in ES cells. FEBS letters 20090806
Insight into a strategy for attenuating AmpC-mediated beta-lactam resistance: structural basis for selective inhibition of the glycoside hydrolase NagZ. Protein science : a publication of the Protein Society 20090701
O-GLcNAc post-translational modifications regulate the entry of neurons into an axon branching program. Developmental neurobiology 20090201
Unique hexosaminidase reduces metabolic survival signal and sensitizes cardiac myocytes to hypoxia/reoxygenation injury. Circulation research 20090102
O-linked beta-N-acetylglucosamine: a new piece of the cardioprotection puzzle? Circulation research 20090102
Elevation of global O-GlcNAc levels in 3T3-L1 adipocytes by selective inhibition of O-GlcNAcase does not induce insulin resistance. The Journal of biological chemistry 20081212
A quantum mechanics/molecular mechanics study of the protein-ligand interaction of two potent inhibitors of human O-GlcNAcase: PUGNAc and NAG-thiazoline. The journal of physical chemistry. B 20081113
The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc. Carbohydrate research 20081103
Increased protein O-GlcNAc modification inhibits inflammatory and neointimal responses to acute endoluminal arterial injury. American journal of physiology. Heart and circulatory physiology 20080701
O-glycosylation of FoxO1 increases its transcriptional activity towards the glucose 6-phosphatase gene. FEBS letters 20080305
Proteomic analysis of O-GlcNAc modifications derived from streptozotocin and glucosamine induced beta-cell apoptosis. Journal of biochemistry and molecular biology 20071130
O-GlcNAc modification modulates the expression of osteocalcin via OSE2 and Runx2. Biochemical and biophysical research communications 20071019
Increased O-GlcNAc levels during reperfusion lead to improved functional recovery and reduced calpain proteolysis. American journal of physiology. Heart and circulatory physiology 20070901
The sweet nature of cardioprotection. American journal of physiology. Heart and circulatory physiology 20070901
Small molecule inhibitors of a glycoside hydrolase attenuate inducible AmpC-mediated beta-lactam resistance. The Journal of biological chemistry 20070720
Glucosamine-induced increase in Akt phosphorylation corresponds to increased endoplasmic reticulum stress in astroglial cells. Molecular and cellular biochemistry 20070401
The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock (Augusta, Ga.) 20070401
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 of the American Chemical Society 20070124
Inhibition of O-GlcNAcase by a gluco-configured nagstatin and a PUGNAc-imidazole hybrid inhibitor. Chemical communications (Cambridge, England) 20061113
Akt1 is dynamically modified with O-GlcNAc following treatments with PUGNAc and insulin-like growth factor-1. FEBS letters 20060529
Structural insights into the mechanism and inhibition of eukaryotic O-GlcNAc hydrolysis. The EMBO journal 20060405
An O-GlcNAcase-specific inhibitor and substrate engineered by the extension of the N-acetyl moiety. Journal of the American Chemical Society 20060405
A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase. Organic & biomolecular chemistry 20060307
Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorganic & medicinal chemistry 20060201
O-GlcNAc modification on IRS-1 and Akt2 by PUGNAc inhibits their phosphorylation and induces insulin resistance in rat primary adipocytes. Experimental & molecular medicine 20050630
Protein O-GlcNAc modulates motility-associated signaling intermediates in neutrophils. The Journal of biological chemistry 20050415
Selective decrease of membrane-associated PKC-alpha and PKC-epsilon in response to elevated intracellular O-GlcNAc levels in transformed human glial cells. Biochimica et biophysica acta 20050415
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. Acta physiologica Scandinavica 20050301
Prolonged incubation in PUGNAc results in increased protein O-Linked glycosylation and insulin resistance in rat skeletal muscle. Diabetes 20040401
Cytosolic O-GlcNAc accumulation is not involved in beta-cell death in HIT-T15 or Min6. Biochemical and biophysical research communications 20010921
O-GlcNAc expression in developing and ageing mouse brain. Biochimie 20010701
Properties