2.0 2012-05-31 14:50:34 -0600 2015-06-03 17:20:18 -0600 ECMDB20558 M2MDB001363 Fructoselysine-6-phosphate Fructoselysine-6-phosphate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Fructoselysine-6-phosphate is invovled in Fructoselysine degradation. Fructoselysine-6-phosphate is involved in the metabolism of fructation product. The metabolism of the glycation product fructose-epsilon-lysine in Escherichia coli involves its ATP-dependent phosphorylation by a specific kinase (FrlD), followed by the conversion of fructoselysine 6-phosphate into glucose 6-phosphate and lysine by fructoselysine-6-phosphate deglycase (FrlB), which is distantly related to the isomerase domain of glucosamine-6-phosphate synthase. (PMID 16153181) Fructoselysine 6-phosphate Fructoselysine 6-phosphoric acid Fructoselysine-6-P Fructoselysine-6-phosphoric acid C12H23N2O10P 386.2922 386.109031478 2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid 2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid NC(CCCCNC1OC(COP(O)(O)=O)C(O)C(O)C1=O)C(O)=O InChI=1S/C12H23N2O10P/c13-6(12(18)19)3-1-2-4-14-11-10(17)9(16)8(15)7(24-11)5-23-25(20,21)22/h6-9,11,14-16H,1-5,13H2,(H,18,19)(H2,20,21,22) BZFCRRVQZCIOBA-UHFFFAOYSA-N Cytosol logp -2.10 ALOGPS logs -1.73 ALOGPS solubility 7.16e+00 g/l ALOGPS logp -8.2 ChemAxon pka_strongest_acidic 1.07 ChemAxon pka_strongest_basic 9.32 ChemAxon iupac 2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid ChemAxon average_mass 386.2922 ChemAxon mono_mass 386.109031478 ChemAxon smiles NC(CCCCNC1OC(COP(O)(O)=O)C(O)C(O)C1=O)C(O)=O ChemAxon formula C12H23N2O10P ChemAxon inchi InChI=1S/C12H23N2O10P/c13-6(12(18)19)3-1-2-4-14-11-10(17)9(16)8(15)7(24-11)5-23-25(20,21)22/h6-9,11,14-16H,1-5,13H2,(H,18,19)(H2,20,21,22) ChemAxon inchikey BZFCRRVQZCIOBA-UHFFFAOYSA-N ChemAxon polar_surface_area 208.87 ChemAxon refractivity 80.45 ChemAxon polarizability 35.8 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Fructoselysine and Psicoselysine Degradation Fructosamines are generated non-enzymatically by a condensation of glucose with primary amines, followed by an Amadori rearrangement. Fructoselysine appears to be metabolized by bacteria in the human hind gut. E. coli can grow on fructoselysine or psicoselysine as the sole carbon source. Growth on fructoselysine induces the production of the enzymes of the fructoselysine degradation pathway. (EcoCyc) PW002049 Metabolic fructoselysine and psicoselysine degradation PWY0-521 Specdb::CMs 1083410 Specdb::EiMs 2565 Specdb::NmrOneD 287875 Specdb::NmrOneD 287876 Specdb::NmrOneD 287877 Specdb::NmrOneD 287878 Specdb::NmrOneD 287879 Specdb::NmrOneD 287880 Specdb::NmrOneD 287881 Specdb::NmrOneD 287882 Specdb::NmrOneD 287883 Specdb::NmrOneD 287884 Specdb::NmrOneD 287885 Specdb::NmrOneD 287886 Specdb::NmrOneD 287887 Specdb::NmrOneD 287888 Specdb::NmrOneD 287889 Specdb::NmrOneD 287890 Specdb::NmrOneD 287891 Specdb::NmrOneD 287892 Specdb::NmrOneD 287893 Specdb::NmrOneD 287894 Specdb::MsMs 26510 Specdb::MsMs 26511 Specdb::MsMs 26512 Specdb::MsMs 33068 Specdb::MsMs 33069 Specdb::MsMs 33070 721 701 FRUCTOSELYSINE-6-PHOSPHATE Keseler, 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. 21097882 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 Wiame, E., Lamosa, P., Santos, H., Van Schaftingen, E. (2005). "Identification of glucoselysine-6-phosphate deglycase, an enzyme involved in the metabolism of the fructation product glucoselysine." Biochem J 392:263-269. 16153181 Fructoselysine 6-phosphate deglycase P0AC00 FRLB_ECOLI frlB http://ecmdb.ca/proteins/P0AC00.xml Fructoselysine kinase P45543 FRLD_ECOLI frlD http://ecmdb.ca/proteins/P45543.xml Fructoselysine-6-phosphate + Water <> Glucose 6-phosphate + L-Lysine RXN0-963 Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate + Hydrogen ion RXN0-962 Fructoselysine-6-phosphate + Water > Glucose 6-phosphate + L-Lysine Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate 1-[(5-Amino-5-carboxypentyl)amino]-1-deoxyfructose + Adenosine triphosphate > Fructoselysine-6-phosphate + ADP + Hydrogen ion PW_R005984 Fructoselysine-6-phosphate + Water <> β-D-glucose 6-phosphate + L-Lysine PW_R005985