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A8625 Sigma

N-Acetyl-D-glucosamine

≥99%

Synonym: 2-Acetamido-2-deoxy-D-glucose, D-GlcNAc

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Properties

Related Categories Biochemicals and Reagents, Carbohydrate Library, Carbohydrates, Carbohydrates A to Z, Carbohydrates A-C,
assay   ≥99%
form   powder
color   white to off-white
mp   211 °C (dec.)(lit.)
solubility   H2O: soluble50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)
storage temp.   −20°C

Description

Application

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N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).

Packaging

10 mg in autosample vial

5, 25 g in poly bottle

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Metabolomic Pathways Chart

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Safety & Documentation

Safety Information

WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

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N-acetyl-β-hexosaminidase--marker of damage to renal proximal tubules. [Article in Polish] Kepka A, Szajda SD, Jankowska A, et al. Pol. Merkur. Lekarski 25, 288-290, (2008)

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Analytical biochemistry and clinical significance of N-acetyl-β-D-glucosaminidase and related enzymes. Muzzarelli RA. EXS 87, 235-247, (1999)

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Activity of N-acetyl-β-hexosaminidase and its isoenzymes A and B in cancer. [Article in Polish] Choromańska B, Luto M, Szajda SD, et al. Postepy Hig. Med. Dosw. (Online) 23, 752-758, (2011)

Characterisation of a secreted N-acetyl-β-hexosaminidase from Trichinella spiralis. Bruce AF, Gounaris K. Mol. Biochem. Parasitol. 145, 84-93, (2006)

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Isoenzymes of N-acetyl-β-hexosaminidase. Zwierz K, Zalewska A, Zoch-Zwierz A. Acta Biochim. Pol. 46, 739-751, (1999)

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O-GlcNAc modification of tau directly inhibits its aggregation without perturbing the conformational properties of tau monomers. Yuzwa SA, Cheung AH, Okon M, et al. J. Mol. Biol. 426(8), 1736-52, (2014)

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Cross-talk between two essential nutrient-sensitive enzymes: O-GlcNAc transferase (OGT) and AMP-activated protein kinase (AMPK). Bullen JW, Balsbaugh JL, Chanda D, et al. J. Biol. Chem. 289(15), 10592-606, (2014)

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Diabetic hyperglycaemia activates CaMKII and arrhythmias by O-linked glycosylation. Erickson JR, Pereira L, Wang L, et al. Nature 502(7471), 372-6, (2013)

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Constant time INEPT CT-HSQC (CTi-CT-HSQC) - A new NMR method to measure accurate one-bond J and RDCs with strong 1H-1H couplings in natural abundance. Yu B, van Ingen H, and Freedberg DI J. Magn. Reson. 228, 159-65, (2013)

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A simple iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides. Weaver LG, Singh Y, Blanchfield JT, et al. Carbohydr. Res. 371, 68-76, (2013)

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Recognition of bisecting N-acetylglucosamine: structural basis for asymmetric interaction with the mouse lectin dendritic cell inhibitory receptor 2. Nagae M, Yamanaka K, Hanashima S, et al. J. Biol. Chem. 288(47), 33598-610, (2013)

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Dual function of the McaS small RNA in controlling biofilm formation. Jørgensen MG, Thomason MK, Havelund J, et al. Genes Dev. 27(10), 1132-45, (2013)

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O-GlcNAc reports ambient temperature and confers heat resistance on ectotherm development. Radermacher PT, Myachina F, Bosshardt F, et al. Proc. Natl. Acad. Sci. U. S. A. 111(15), 5592-7, (2014)

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Increased sugar uptake promotes oncogenesis via EPAC/RAP1 and O-GlcNAc pathways. Onodera Y, Nam JM, and Bissell MJ J. Clin. Invest. 124(1), 367-84, (2014)

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Sugarcoating Polycomb repression. Verrijzer CP Dev. Cell 31(5), 521-2, (2014)

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O-GlcNAcylation prevents aggregation of the Polycomb group repressor polyhomeotic. Gambetta MC and Müller J Dev. Cell 31(5), 629-39, (2014)

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Enzyme processivity changes with the extent of recalcitrant polysaccharide degradation. Hamre AG, Lorentzen SB, Väljamäe P, et al. FEBS Lett. 588(24), 4620-4, (2014)

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Exploring NAG-thiazoline and its derivatives as inhibitors of chitinolytic β-acetylglucosaminidases. Liu T, Xia M, Zhang H, et al. FEBS Lett. 589(1), 110-6, (2015)

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Sugar modification inhibits autophagosome-lysosome fusion. Mizushima N Nat. Cell Biol. 16(12), 1132-3, (2014)

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O-GlcNAc-modification of SNAP-29 regulates autophagosome maturation. Guo B, Liang Q, Li L, et al. Nat. Cell Biol. 16(12), 1215-26, (2014)

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The emerging link between O-GlcNAc and Alzheimer disease. Zhu Y, Shan X, Yuzwa SA, et al. J. Biol. Chem. 289(50), 34472-81, (2014)

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O-GlcNAc and the epigenetic regulation of gene expression. Lewis BA and Hanover JA J. Biol. Chem. 289(50), 34440-8, (2014)

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Multiple tissue-specific roles for the O-GlcNAc post-translational modification in the induction of and complications arising from type II diabetes. Vaidyanathan K and Wells L J. Biol. Chem. 289(50), 34466-71, (2014)

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O-GlcNAcase: promiscuous hexosaminidase or key regulator of O-GlcNAc signaling? Alonso J, Schimpl M, and van Aalten DM J. Biol. Chem. 289(50), 34433-9, (2014)

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Minireview series on the thirtieth anniversary of research on O-GlcNAcylation of nuclear and cytoplasmic proteins: Nutrient regulation of cellular metabolism and physiology by O-GlcNAcylation. Hart GW J. Biol. Chem. 289(50), 34422-3, (2014)

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Cancer metabolism and elevated O-GlcNAc in oncogenic signaling. Ma Z and Vosseller K J. Biol. Chem. 289(50), 34457-65, (2014)

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Protein O-GlcNAcylation and cardiovascular (patho)physiology. Marsh SA, Collins HE, and Chatham JC J. Biol. Chem. 289(50), 34449-56, (2014)

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Increased O-GlcNAc levels correlate with decreased O-GlcNAcase levels in Alzheimer disease brain. Förster S, Welleford AS, Triplett JC, et al. Biochim. Biophys. Acta 1842(9), 1333-9, (2014)

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Dynamic O-linked N-acetylglucosamine modification of proteins affects stress responses and survival of mesothelial cells exposed to peritoneal dialysis fluids. Herzog R, Bender TO, Vychytil A, et al. J. Am. Soc. Nephrol. 25(12), 2778-88, (2014)

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O-GlcNAc signaling in cancer metabolism and epigenetics. Singh JP, Zhang K, Wu J, et al. Cancer Lett. 356(2 Pt A), 244-50, (2015)

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[Thromboresistance of glucose-containing hydrogels]. Valuev IL, Valuev LI, Vanchugova LV, et al. Prikl. Biokhim. Mikrobiol. 49(3), 319-21, (2013)

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[Role of the O-linked beta-N-acetylglucosamine in the cardioprotection induced by isoflurane]. Hirose K, Tsutsumi Y, Tanaka K, et al. Masui. 61 Suppl, S152-8, (2012)

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[Bio-based pharmaceutical polymers, possibility of their chemical modification and the applicability of modified polymers]. Sebe I, Szabó B, and Zelkó R Acta Pharm. Hung. 82(4), 138-54, (2012)

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Introduction to informatics in glycoprotein analysis. Aoki-Kinoshita KF Methods Mol. Biol. 951, 257-67, (2013)

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Approaches for site mapping and quantification of O-linked glycopeptides. Zhao P, Stalnaker SH, and Wells L Methods Mol. Biol. 951, 229-44, (2013)

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Incorporation of unnatural sugars for the identification of glycoproteins. Zaro BW, Hang HC, and Pratt MR Methods Mol. Biol. 951, 57-67, (2013)

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Tandem lectin weak affinity chromatography for glycoprotein enrichment. Ma ZY, Skorobogatko Y, and Vosseller K Methods Mol. Biol. 951, 21-31, (2013)

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Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins. Hart GW, Housley MP, and Slawson C Nature 446(7139), 1017-22, (2007)

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N-acetylglucosamine: a new osmotic solute in peritoneal dialysis solutions. Breborowicz A, Wieczorowska-Tobis K, Kuzlan M, et al. Perit. Dial. Int. 17 Suppl 2, S80-3, (1997)

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Antibody to a conserved antigenic target is protective against diverse prokaryotic and eukaryotic pathogens. Cywes-Bentley C, Skurnik D, Zaidi T, et al. Proc. Natl. Acad. Sci. U. S. A. 110(24), E2209-18, (2013)

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Hyaluronan synthase 1 (HAS1) requires higher cellular UDP-GlcNAc concentration than HAS2 and HAS3. Rilla K, Oikari S, Jokela TA, et al. J. Biol. Chem. 288(8), 5973-83, (2013)

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[Studies on "mannan-binding proteins," mammalian lectin specific for mannose and N-acetylglucosamine residues]. Kawasaki T Seikagaku. 54(9), 1019-32, (1982)

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Proteome wide purification and identification of O-GlcNAc-modified proteins using click chemistry and mass spectrometry. Hahne H, Sobotzki N, Nyberg T, et al. J. Proteome Res. 12(2), 927-36, (2013)

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Glycan-dependent signaling: O-linked N-acetylglucosamine. Hanover JA FASEB J. 15(11), 1865-76, (2001)

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N-acetyl-D-glucosamine-induced morphogenesis in Candida albicans. Cassone A, Sullivan PA, and Shepherd MG Microbiologica 8(1), 85-99, (1985)

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Imaging and therapy of liver fibrosis using bioreducible polyethylenimine/siRNA complexes conjugated with N-acetylglucosamine as a targeting moiety. Kim SJ, Ise H, Kim E, et al. Biomaterials 34(27), 6504-14, (2013)

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Protein O-linked β-N-acetylglucosamine: a novel effector of cardiomyocyte metabolism and function. Darley-Usmar VM, Ball LE, and Chatham JC J. Mol. Cell. Cardiol. 52(3), 538-49, (2012)

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N-acetylglucosamine: production and applications. Chen JK, Shen CR, and Liu CL Mar. Drugs 8(9), 2493-516, (2010)

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O-linked N-acetylglucosamine and cancer: messages from the glycosylation of c-Myc. Chou TY and Hart GW Adv. Exp. Med. Biol. 491, 413-8, (2001)

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The roles of O-linked β-N-acetylglucosamine in cardiovascular physiology and disease. Zachara NE Am. J. Physiol. Heart Circ. Physiol. 302(10), H1905-18, (2012)

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A role for N-acetylglucosamine as a nutrient sensor and mediator of insulin resistance. Wells L, Vosseller K, and Hart GW Cell. Mol. Life Sci. 60(2), 222-8, (2003)

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O-linked β-N-acetylglucosamine (O-GlcNAc): Extensive crosstalk with phosphorylation to regulate signaling and transcription in response to nutrients and stress. Butkinaree C, Park K, Hart GW. Biochim. Biophys. Acta 1800, 96-106, (2010)

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A novel ion-exclusion chromatography-mass spectrometry method to measure concentrations and cycling rates of carbohydrates and amino sugars in freshwaters. Horňák K and Pernthaler J J. Chromatogr. A 1365, 115-23, (2014)

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The role of protein O-linked beta-N-acetylglucosamine in mediating cardiac stress responses. Chatham JC and Marchase RB Biochim. Biophys. Acta 1800(2), 57-66, (2010)

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Quantitative regulation of nuclear pore complex proteins by O-GlcNAcylation. Mizuguchi-Hata C, Ogawa Y, Oka M, et al. Biochim. Biophys. Acta 1833(12), 2682-9, (2013)

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Triptolide-induced cell death in pancreatic cancer is mediated by O-GlcNAc modification of transcription factor Sp1. Banerjee S, Sangwan V, McGinn O, et al. J. Biol. Chem. 288(47), 33927-38, (2013)

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The O-linked N-acetylglucosamine modification in cellular signalling and the immune system. 'Protein modifications: beyond the usual suspects' review series. Golks A and Guerini D EMBO Rep. 9(8), 748-53, (2008)

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Microbial production of glucosamine and N-acetylglucosamine: advances and perspectives. Liu L, Liu Y, Shin HD, et al. Appl. Microbiol. Biotechnol. 97(14), 6149-58, (2013)

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New insights into metabolic signaling and cell survival: the role of beta-O-linkage of N-acetylglucosamine. Ngoh GA and Jones SP J. Pharmacol. Exp. Ther. 327(3), 602-9, (2008)

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O-Linked β-N-acetylglucosamine (O-GlcNAc) regulates emerin binding to barrier to autointegration factor (BAF) in a chromatin- and lamin B-enriched "niche". Berk JM, Maitra S, Dawdy AW, et al. J. Biol. Chem. 288(42), 30192-209, (2013)

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Discovery of β-1,4-D-mannosyl-N-acetyl-D-glucosamine phosphorylase involved in the metabolism of N-glycans. Nihira T, Suzuki E, Kitaoka M, et al. J. Biol. Chem. 288(38), 27366-74, (2013)

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The DMAP interaction domain of UDP-GlcNAc:lysosomal enzyme N-acetylglucosamine-1-phosphotransferase is a substrate recognition module. Qian Y, Flanagan-Steet H, van Meel E, et al. Proc. Natl. Acad. Sci. U. S. A. 110(25), 10246-51, (2013)

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TraG encoded by the pIP501 type IV secretion system is a two-domain peptidoglycan-degrading enzyme essential for conjugative transfer. Arends K, Celik EK, Probst I, et al. J. Bacteriol. 195(19), 4436-44, (2013)

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O-GlcNAcylation at promoters, nutrient sensors, and transcriptional regulation. Lewis BA Biochim. Biophys. Acta 1829(11), 1202-6, (2013)

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Circadian regulation of metabolism. Bailey SM, Udoh US, and Young ME J. Endocrinol. 222(2), R75-96, (2014)

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O-GlcNAc modification of the coat protein of the potyvirus Plum pox virus enhances viral infection. Pérez Jde J, Udeshi ND, Shabanowitz J, et al. Virology 442(2), 122-31, (2013)

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GTDC2 modifies O-mannosylated α-dystroglycan in the endoplasmic reticulum to generate N-acetyl glucosamine epitopes reactive with CTD110.6 antibody. Ogawa M, Nakamura N, Nakayama Y, et al. Biochem. Biophys. Res. Commun. 440(1), 88-93, (2013)

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Antibodies that detect O-linked β-D-N-acetylglucosamine on the extracellular domain of cell surface glycoproteins. Tashima Y and Stanley P J. Biol. Chem. 289(16), 11132-42, (2014)

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Z-band alternatively spliced PDZ motif protein (ZASP) is the major O-linked β-N-acetylglucosamine-substituted protein in human heart myofibrils. Leung MC, Hitchen PG, Ward DG, et al. J. Biol. Chem. 288(7), 4891-8, (2013)

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Production of N-acetyl-D-neuraminic acid using two sequential enzymes overexpressed as double-tagged fusion proteins. Tzu-Hsien Wang et al BMC Biotechnol. 9, 63, (2009)

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Serum GlcNAc-binding IgM of fugu (Takifugu rubripes) suppresses the growth of fish pathogenic bacteria: a novel function of teleost antibody. Tsutsui S, Ariji T, Sato A, et al. Dev. Comp. Immunol. 41(1), 20-6, (2013)

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Implications of the O-GlcNAc modification in the regulation of nuclear apoptosis in T cells. Johnson B, Opimba M, and Bernier J Biochim. Biophys. Acta 1840(1), 191-8, (2014)

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Basigin null mutant male mice are sterile and exhibit impaired interactions between germ cells and Sertoli cells. Bi J, Li Y, Sun F, et al. Dev. Biol. 380(2), 145-56, (2013)

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Chemical tools to probe cellular O-GlcNAc signalling. Ostrowski A and van Aalten DM Biochem. J. 456(1), 1-12, (2013)

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Cross-functionalities of Bacillus deacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways. Fang Z, Roberts AA, Weidman K, et al. Biochem. J. 454(2), 239-47, (2013)

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Use of novel mutant galactosyltransferase for the bioconjugation of terminal N-acetylglucosamine (GlcNAc) residues on live cell surface. Mercer N, Ramakrishnan B, Boeggeman E, et al. Bioconjug. Chem. 24(1), 144-52, (2013)

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O-GlcNAcylation of cofilin promotes breast cancer cell invasion. Huang X, Pan Q, Sun D, et al. J. Biol. Chem. 288(51), 36418-25, (2013)

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O-linked N-acetylglucosamine cycling regulates mitotic spindle organization. Tan EP, Caro S, Potnis A, et al. J. Biol. Chem. 288(38), 27085-99, (2013)

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A correlation between altered O-GlcNAcylation, migration and with changes in E-cadherin levels in ovarian cancer cells. Jin FZ, Yu C, Zhao DZ, et al. Exp. Cell Res. 319(10), 1482-90, (2013)

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Short-chain fatty acid-modified hexosamine for tissue-engineering osteoarthritic cartilage. Coburn JM, Wo L, Bernstein N, et al. Tissue Eng. Part A 19(17-18), 2035-44, (2013)

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Generation and characterization of a rabbit monoclonal antibody site-specific for tau O-GlcNAcylated at serine 400. Cameron A, Giacomozzi B, Joyce J, et al. FEBS Lett. 587(22), 3722-8, (2013)

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Wide-angle X-ray solution scattering for protein-ligand binding: multivariate curve resolution with Bayesian confidence intervals. Minh DD and Makowski L Biophys. J. 104(4), 873-83, (2013)

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Biochemical analysis and structure determination of bacterial acetyltransferases responsible for the biosynthesis of UDP-N,N'-diacetylbacillosamine. Morrison MJ and Imperiali B J. Biol. Chem. 288(45), 32248-60, (2013)

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Collagen-induced arthritis: severity and immune response attenuation using multivalent N-acetyl glucosamine. Richter J, Capková K, Hříbalová V, et al. Clin. Exp. Immunol. 177(1), 121-33, (2014)

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Functional diversification of cerato-platanins in Moniliophthora perniciosa as seen by differential expression and protein function specialization. de O Barsottini MR, de Oliveira JF, Adamoski D, et al. Mol. Plant Microbe Interact. 26(11), 1281-93, (2013)

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Preparation of hyaluronan polyaldehyde-a precursor of biopolymer conjugates. Šedová P, Buffa R, Kettou S, et al. Carbohydr. Res. 371, 8-15, (2013)

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In vitro comparative evaluation of the impact of lacto-N-biose I, a major building block of human milk oligosaccharides, on the fecal microbiota of infants. Satoh T, Odamaki T, Namura M, et al. Anaerobe 19, 50-7, (2013)

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MotiveValidator: interactive web-based validation of ligand and residue structure in biomolecular complexes. Vařeková RS, Jaiswal D, Sehnal D, et al. Nucleic Acids Res. 42(Web Server issue), W227-33, (2014)

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Adipogenesis stimulates the nuclear localization of EWS with an increase in its O-GlcNAc glycosylation in 3T3-L1 cells. Li Q and Kamemura K Biochem. Biophys. Res. Commun. 450(1), 588-92, (2014)

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Partially acetylated chitooligosaccharides bind to YKL-40 and stimulate growth of human osteoarthritic chondrocytes. Einarsson JM, Bahrke S, Sigurdsson BT, et al. Biochem. Biophys. Res. Commun. 434(2), 298-304, (2013)

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O-GlcNAcylation of BMAL1 regulates circadian rhythms in NIH3T3 fibroblasts. Ma YT, Luo H, Guan WJ, et al. Biochem. Biophys. Res. Commun. 431(3), 382-7, (2013)

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High glucose-induced O-GlcNAcylated carbohydrate response element-binding protein (ChREBP) mediates mesangial cell lipogenesis and fibrosis: the possible role in the development of diabetic nephropathy. Park MJ, Kim DI, Lim SK, et al. J. Biol. Chem. 289(19), 13519-30, (2014)

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Plasmodium falciparum: generation of pure gametocyte culture by heparin treatment. Miao J, Wang Z, Liu M, et al. Exp. Parasitol. 135(3), 541-5, (2013)

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Requirement of decreased O-GlcNAc glycosylation of Mef2D for its recruitment to the myogenin promoter. Ogawa M, Sakakibara Y, and Kamemura K Biochem. Biophys. Res. Commun. 433(4), 558-62, (2013)

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MADP, a salidroside analog, protects hippocampal neurons from glutamate induced apoptosis. Xian H, Zhao J, Zheng Y, et al. Life Sci. 103(1), 34-40, (2014)

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Acidobacteria from oligotrophic soil from the Cerrado can grow in a wide range of carbon source concentrations. de Castro VH, Schroeder LF, Quirino BF, et al. Can. J. Microbiol. 59(11), 746-53, (2013)

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O-linked N-acetylglucosamine: the "yin-yang" of Ser/Thr phosphorylation? Nuclear and cytoplasmic glycosylation. Hart GW, Greis KD, Dong LY, et al. Adv. Exp. Med. Biol. 376, 115-23, (1995)

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Comparative Biochemistry of Molecular Targets for Drug and Pesticides: N-acetyl-D-glucosamine and Acetylcholine Related Enzymes. Yang QY. Curr. Drug Targets 13(4), 441, (2012)

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Merck 14,4458

Beil. 4,IV,2036

FT-IR 1 (1), 757:D / FT-IR 2 (1), 1276:C / FT-NMR 1 (1), 1238:A / IR-Spectra (3), 442:H / IR-Spectra (2), 392:A / NMR-Reference 2 (1), 638:C / RegBook 1 (1), 889:E / Sigma FT-IR 1 (1), 1031:D / Structure Index 1, 136:B:6

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