2.0 2012-05-31 14:50:31 -0600 2015-06-07 12:23:21 -0600 ECMDB20557 M2MDB001362 Fructoselysine Fructoselysine 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 is invovled in Fructoselysine degradation. Escherichia coli was found to grow on fructoselysine as an energetic substrate at a rate of about one-third of that observed with glucose. (PMID:12147680) Fructoselysine Psicoselysine C12H22N2O7 306.3123 306.142701068 2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid 2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid NC(CCCCNC1OC(CO)C(O)C(O)C1=O)C(O)=O InChI=1S/C12H22N2O7/c13-6(12(19)20)3-1-2-4-14-11-10(18)9(17)8(16)7(5-15)21-11/h6-9,11,14-17H,1-5,13H2,(H,19,20) ZRMPOBPOYIGDMF-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp -2.78 ALOGPS logs -0.66 ALOGPS solubility 6.73e+01 g/l ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 1.58 ChemAxon pka_strongest_basic 9.27 ChemAxon iupac 2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid ChemAxon average_mass 306.3123 ChemAxon mono_mass 306.142701068 ChemAxon smiles NC(CCCCNC1OC(CO)C(O)C(O)C1=O)C(O)=O ChemAxon formula C12H22N2O7 ChemAxon inchi InChI=1S/C12H22N2O7/c13-6(12(19)20)3-1-2-4-14-11-10(18)9(17)8(16)7(5-15)21-11/h6-9,11,14-17H,1-5,13H2,(H,19,20) ChemAxon inchikey ZRMPOBPOYIGDMF-UHFFFAOYSA-N ChemAxon polar_surface_area 162.34 ChemAxon refractivity 69.57 ChemAxon polarizability 31.07 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge 0 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 1083395 Specdb::EiMs 3057 Specdb::NmrOneD 285555 Specdb::NmrOneD 285556 Specdb::NmrOneD 285557 Specdb::NmrOneD 285558 Specdb::NmrOneD 285559 Specdb::NmrOneD 285560 Specdb::NmrOneD 285561 Specdb::NmrOneD 285562 Specdb::NmrOneD 285563 Specdb::NmrOneD 285564 Specdb::NmrOneD 285565 Specdb::NmrOneD 285566 Specdb::NmrOneD 285567 Specdb::NmrOneD 285568 Specdb::NmrOneD 285569 Specdb::NmrOneD 285570 Specdb::NmrOneD 285571 Specdb::NmrOneD 285572 Specdb::NmrOneD 285573 Specdb::NmrOneD 285574 Specdb::MsMs 22985 Specdb::MsMs 22986 Specdb::MsMs 22987 Specdb::MsMs 29783 Specdb::MsMs 29784 Specdb::MsMs 29785 720 700 C16488 FRUCTOSELYSINE 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 Fructoselysine kinase P45543 FRLD_ECOLI frlD http://ecmdb.ca/proteins/P45543.xml Putative fructoselysine transporter frlA P45539 FRLA_ECOLI frlA http://ecmdb.ca/proteins/P45539.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Protein frlC P45541 FRLC_ECOLI frlC http://ecmdb.ca/proteins/P45541.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 Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate + Hydrogen ion RXN0-962 Fructoselysine <> Fructoselysine RXN0-4841 Fructoselysine <> Fructoselysine RXN0-4841 Adenosine triphosphate + Fructoselysine > ADP + Fructoselysine-6-phosphate Fructoselysine <> 1-[(5-Amino-5-carboxypentyl)amino]-1-deoxyfructose PW_R005983