2.02012-05-31 10:23:52 -06002015-09-13 12:56:07 -0600ECMDB00215M2MDB000088N-Acetyl-D-glucosamineN-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. 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 initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. (PMID 16237703)2-(Acetylamino)-2-deoxyhexose2-Acetamido-2-deoxy-D-glucose2-Acetamido-2-deoxyglucose2-Acetamido-D-glucose2-Acetylamino-2-deoxy-D-glucose<i>N</i>-acetylglucosamineAcetylglucosamineGlcnacN-AcetylchitosamineN-AcetylglucosamineNAcGlcC8H15NO6221.2078221.089937217N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideN-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide7512-17-6[H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1OVRNDRQMDRJTHS-DMHSOCPYSA-NSolidCytosolExtra-organismPeriplasmlogp-2.60logs0.06solubility2.54e+02 g/lmelting_point210 oClogp-3.2pka_strongest_acidic11.6pka_strongest_basic-0.78iupacN-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamideaverage_mass221.2078mono_mass221.089937217smiles[H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]formulaC8H15NO6inchiInChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1inchikeyOVRNDRQMDRJTHS-DMHSOCPYSA-Npolar_surface_area119.25refractivity47.02polarizability20.6rotatable_bond_count2acceptor_count6donor_count5physiological_charge0formal_charge0Amino sugar and nucleotide sugar metabolismec00520Phosphotransferase system (PTS)ec02060ABC transportersec02010chitobiose degradationPWY0-1309Specdb::NmrOneD1209Specdb::MsMs352Specdb::MsMs353Specdb::MsMs354Specdb::MsMs1255024Specdb::MsMs1255025Specdb::MsMs1255026Specdb::MsMs1370227Specdb::MsMs1370228Specdb::MsMs1370229Specdb::NmrTwoD997Specdb::NmrTwoD1213HMDB0021543917410035566C0014017411N-ACETYL-D-GLUCOSAMINENGZN-acetylglucosamineKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Slawson, C., Housley, M. P., Hart, G. W. (2006). "O-GlcNAc cycling: how a single sugar post-translational modification is changing the way we think about signaling networks." J Cell Biochem 97:71-83.16237703Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp. http://hmdb.ca/system/metabolites/msds/000/000/153/original/HMDB00215.pdf?1358895005Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlProbable bifunctional chitinase/lysozymeP13656CHIA_ECOLIchiAhttp://ecmdb.ca/proteins/P13656.xml6-phospho-beta-glucosidaseP17411CHBF_ECOLIchbFhttp://ecmdb.ca/proteins/P17411.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlBeta-hexosaminidaseP75949NAGZ_ECOLInagZhttp://ecmdb.ca/proteins/P75949.xmlN-acetyl-D-glucosamine kinaseP75959NAGK_ECOLInagKhttp://ecmdb.ca/proteins/P75959.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlProbable bifunctional chitinase/lysozymeP13656CHIA_ECOLIchiAhttp://ecmdb.ca/proteins/P13656.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlPhosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acidTRANS-RXN-167N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramateN-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptideN-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptideN-Acetyl-D-glucosamine + Adenosine triphosphate <> N-Acetyl-D-Glucosamine 6-Phosphate + ADP + Hydrogen ionR01201N-ACETYLGLUCOSAMINE-KINASE-RXNDiacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-PhosphateRXN0-5243Chitobiose + Water <>2 N-Acetyl-D-glucosamineR00022Adenosine triphosphate + N-Acetyl-D-glucosamine <> ADP + N-Acetyl-D-Glucosamine 6-PhosphateR01201Chitin + Water <> N-Acetyl-D-glucosamine + ChitinR01206Protein N(pi)-phospho-L-histidine + N-Acetyl-D-glucosamine <> Protein histidine + N-Acetyl-D-Glucosamine 6-PhosphateR05199a peptidoglycan + Water a peptidoglycan with cleaved N-acetyl-glucosamine + N-Acetyl-D-glucosamine3.2.1.17-RXNN-Acetyl-D-glucosamine + Adenosine triphosphate > Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADPR01201N-ACETYLGLUCOSAMINE-KINASE-RXN<i>N</i>-acetyl-β-D-glucosamine(anhydrous)-<i>N</i>-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramateRXN0-5226Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acidTRANS-RXN-167Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ionTRANS-RXN0-210Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ionTRANS-RXN0-210Chitobiose + Water <>2 N-Acetyl-D-glucosamineChitobiose + Water <>2 N-Acetyl-D-glucosamine