2.0 2012-05-31 13:53:46 -0600 2015-10-23 17:32:16 -0600 ECMDB01514 M2MDB000406 Glucosamine Glucosamine (C6H14NO5) is an amino sugar that is an important precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is one of the most abundant monosaccharides. (Wikipedia) 2-Amino-2-deoxy-D-glucopyranose 2-Amino-2-deoxy-D-Glucose 2-Amino-2-deoxyglucose 2-Aminoglucose 2-Deoxy-2-amino-D-glucose 2-Deoxy-2-aminoglucose Chitosamine Cosamin D-(+)-Glucosamine D-Glucosamine Glucosamine C6H13NO5 179.1711 179.079372531 (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol glucosamine 3416-24-8 N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 MSWZFWKMSRAUBD-IVMDWMLBSA-N Solid Extra-organism Periplasm logp -2.73 ALOGPS logs 0.49 ALOGPS solubility 5.51e+02 g/l ALOGPS melting_point 88 oC logp -3 ChemAxon pka_strongest_acidic 11.73 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol ChemAxon average_mass 179.1711 ChemAxon mono_mass 179.079372531 ChemAxon smiles N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1 ChemAxon inchikey MSWZFWKMSRAUBD-IVMDWMLBSA-N ChemAxon polar_surface_area 116.17 ChemAxon refractivity 37.58 ChemAxon polarizability 16.87 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 Specdb::CMs 17655 Specdb::CMs 38103 Specdb::CMs 132620 Specdb::CMs 140354 Specdb::NmrOneD 96358 Specdb::NmrOneD 96359 Specdb::NmrOneD 96360 Specdb::NmrOneD 96361 Specdb::NmrOneD 96362 Specdb::NmrOneD 96363 Specdb::NmrOneD 96364 Specdb::NmrOneD 96365 Specdb::NmrOneD 96366 Specdb::NmrOneD 96367 Specdb::NmrOneD 96368 Specdb::NmrOneD 96369 Specdb::NmrOneD 96370 Specdb::NmrOneD 96371 Specdb::NmrOneD 96372 Specdb::NmrOneD 96373 Specdb::NmrOneD 96374 Specdb::NmrOneD 96375 Specdb::NmrOneD 96376 Specdb::NmrOneD 96377 Specdb::MsMs 75216 Specdb::MsMs 75217 Specdb::MsMs 75218 Specdb::MsMs 134817 Specdb::MsMs 134818 Specdb::MsMs 134819 Specdb::MsMs 1218130 Specdb::MsMs 1218131 Specdb::MsMs 1218132 Specdb::MsMs 2226560 Specdb::MsMs 2228186 Specdb::MsMs 2228961 Specdb::MsMs 2230465 Specdb::MsMs 2231300 Specdb::MsMs 2232921 Specdb::MsMs 2233612 Specdb::MsMs 2235306 Specdb::MsMs 2236469 Specdb::MsMs 2236892 Specdb::MsMs 2238580 Specdb::MsMs 2239018 Specdb::MsMs 2240674 Specdb::MsMs 2241001 Specdb::MsMs 2242794 Specdb::MsMs 2243064 Specdb::NmrTwoD 2013 Specdb::NmrTwoD 2014 HMDB01514 439213 C00329 17315 GLUCOSAMINE Glucosamine Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Li, Nan; Li, Jiheng. Preparation of D-glucosamine hydrochloride. Zhongguo Yaoke Daxue Xuebao (1997), 28(1), 56-58. http://hmdb.ca/system/metabolites/msds/000/001/373/original/Glucosamine_MSDS.pdf?1368648101 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + Glucosamine > Glucosamine 6-phosphate + Pyruvic acid TRANS-RXN-167A Glucosamine + Phosphoenolpyruvic acid > Glucosamine 6-phosphate + Pyruvic acid TRANS-RXN-167A 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 19.2 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 76800 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776