2.02012-05-31 13:53:46 -06002015-10-23 17:32:16 -0600ECMDB01514M2MDB000406GlucosamineGlucosamine (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-glucopyranose2-Amino-2-deoxy-D-Glucose2-Amino-2-deoxyglucose2-Aminoglucose2-Deoxy-2-amino-D-glucose2-Deoxy-2-aminoglucoseChitosamineCosaminD-(+)-GlucosamineD-GlucosamineGlucosamineC6H13NO5179.1711179.079372531(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triolglucosamine3416-24-8N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1OInChI=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/s1MSWZFWKMSRAUBD-IVMDWMLBSA-NSolidExtra-organismPeriplasmlogp-2.73logs0.49solubility5.51e+02 g/lmelting_point88 oClogp-3pka_strongest_acidic11.73pka_strongest_basic8.23iupac(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triolaverage_mass179.1711mono_mass179.079372531smilesN[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1OformulaC6H13NO5inchiInChI=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/s1inchikeyMSWZFWKMSRAUBD-IVMDWMLBSA-Npolar_surface_area116.17refractivity37.58polarizability16.87rotatable_bond_count1acceptor_count6donor_count5physiological_charge1formal_charge0Amino sugar and nucleotide sugar metabolismec00520Phosphotransferase system (PTS)ec02060Specdb::CMs17655Specdb::CMs38103Specdb::CMs132620Specdb::CMs140354Specdb::NmrOneD96358Specdb::NmrOneD96359Specdb::NmrOneD96360Specdb::NmrOneD96361Specdb::NmrOneD96362Specdb::NmrOneD96363Specdb::NmrOneD96364Specdb::NmrOneD96365Specdb::NmrOneD96366Specdb::NmrOneD96367Specdb::NmrOneD96368Specdb::NmrOneD96369Specdb::NmrOneD96370Specdb::NmrOneD96371Specdb::NmrOneD96372Specdb::NmrOneD96373Specdb::NmrOneD96374Specdb::NmrOneD96375Specdb::NmrOneD96376Specdb::NmrOneD96377Specdb::MsMs75216Specdb::MsMs75217Specdb::MsMs75218Specdb::MsMs134817Specdb::MsMs134818Specdb::MsMs134819Specdb::MsMs1218130Specdb::MsMs1218131Specdb::MsMs1218132Specdb::MsMs2226560Specdb::MsMs2228186Specdb::MsMs2228961Specdb::MsMs2230465Specdb::MsMs2231300Specdb::MsMs2232921Specdb::MsMs2233612Specdb::MsMs2235306Specdb::MsMs2236469Specdb::MsMs2236892Specdb::MsMs2238580Specdb::MsMs2239018Specdb::MsMs2240674Specdb::MsMs2241001Specdb::MsMs2242794Specdb::MsMs2243064Specdb::NmrTwoD2013Specdb::NmrTwoD2014HMDB01514439213C0032917315GLUCOSAMINEGlucosamineKanehisa, 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 80:2939-2948.18331064Ishii, 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 316:593-597.17379776Li, 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?1368648101Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlPTS system mannose-specific EIIAB componentP69797PTNAB_ECOLImanXhttp://ecmdb.ca/proteins/P69797.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlMannose permease IIC componentP69801PTNC_ECOLImanYhttp://ecmdb.ca/proteins/P69801.xmlMannose permease IID componentP69805PTND_ECOLImanZhttp://ecmdb.ca/proteins/P69805.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 + Glucosamine > Glucosamine 6-phosphate + Pyruvic acidTRANS-RXN-167AGlucosamine + Phosphoenolpyruvic acid > Glucosamine 6-phosphate + Pyruvic acidTRANS-RXN-167A48 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h19.2uM0.037 oCBW25113Stationary Phase, glucose limited768000Ishii, 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