2.0 2012-05-31 14:30:57 -0600 2015-09-17 15:42:02 -0600 ECMDB20165 M2MDB001012 L-Fuculose 1-phosphate L-fuculose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. (PMID 17709419) 6-Deoxy-1-O-phosphono-L-tagatose 6-Deoxy-L-lyxo-hex-2-ulose 1-(dihydrogen phosphate) 6-Deoxy-L-lyxo-hex-2-ulose 1-(dihydrogen phosphoric acid) 6-Deoxy-L-tagatose 1-(dihydrogen phosphate) 6-Deoxy-L-tagatose 1-(dihydrogen phosphoric acid) Fuculose-1-P Fuculose-1-phosphate Fuculose-1-phosphoric acid Fuculose1P L-Fuculose 1-phosphoric acid L-Fuculose-1-P Rhamnulose 1-phosphate Rhamnulose 1-phosphoric acid C6H11O8P 242.121 242.020251472 {[(3R,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid L-fuculose 1-phosphate 92418-41-2 CC(O)C(O)C(O)C(=O)COP([O-])([O-])=O InChI=1S/C6H13O8P/c1-3(7)5(9)6(10)4(8)2-14-15(11,12)13/h3,5-7,9-10H,2H2,1H3,(H2,11,12,13)/p-2 KNYGWWDTPGSEPD-UHFFFAOYSA-L Cytosol logp -1.86 ALOGPS logs -0.99 ALOGPS solubility 2.49e+01 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 1.18 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac {[(3R,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid ChemAxon average_mass 242.121 ChemAxon mono_mass 242.020251472 ChemAxon smiles CC(O)C(O)C(O)C(=O)COP([O-])([O-])=O ChemAxon formula C6H11O8P ChemAxon inchi InChI=1S/C6H13O8P/c1-3(7)5(9)6(10)4(8)2-14-15(11,12)13/h3,5-7,9-10H,2H2,1H3,(H2,11,12,13)/p-2 ChemAxon inchikey KNYGWWDTPGSEPD-UHFFFAOYSA-L ChemAxon polar_surface_area 144.52 ChemAxon refractivity 46.89 ChemAxon polarizability 20.05 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Microbial metabolism in diverse environments ec01120 fucose and rhamnose degradation In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Via reactions catalyzed by proteins encoded in linked operons comprising a regulon, the methylpentose, alpha-L-rhamnopyranose and/or beta-L-rhamnopyranose, is taken into the cell through a proton symporter and metabolized, enabling E. coli to grow on it as a total source of carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can be used for degradation of L-lactaldehyde. Aerobically, it is converted via lactate to pyruvate, also an intermediate of glycolysis. Anaerobically, lactaldehyde reductase is induced which converts lactaldehyde into propane-1,2-diol. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment. PW000826 Metabolic fucose degradation FUCCAT-PWY Specdb::MsMs 24893 Specdb::MsMs 24894 Specdb::MsMs 24895 Specdb::MsMs 31451 Specdb::MsMs 31452 Specdb::MsMs 31453 6857415 5256754 C01099 16647 FUCULOSE-1P 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 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 Autieri, S. M., Lins, J. J., Leatham, M. P., Laux, D. C., Conway, T., Cohen, P. S. (2007). "L-fucose stimulates utilization of D-ribose by Escherichia coli MG1655 DeltafucAO and E. coli Nissle 1917 DeltafucAO mutants in the mouse intestine and in M9 minimal medium." Infect Immun 75:5465-5475. 17709419 L-fuculose phosphate aldolase P0AB87 FUCA_ECOLI fucA http://ecmdb.ca/proteins/P0AB87.xml L-fuculokinase P11553 FUCK_ECOLI fucK http://ecmdb.ca/proteins/P11553.xml Putative aldolase class 2 protein ygbL Q46890 YGBL_ECOLI ygbL http://ecmdb.ca/proteins/Q46890.xml L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde R02262 FUCPALDOL-RXN Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate + Hydrogen ion R03241 FUCULOKIN-RXN L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde R02262 Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate R03241 L-Fuculose + Adenosine triphosphate > Hydrogen ion + L-Fuculose 1-phosphate + ADP FUCULOKIN-RXN L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde Adenosine triphosphate + L-Fuculose > ADP + L-Fuculose 1-phosphate L-fuculose 1-phosphate + L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde PW_R002972 Adenosine triphosphate + keto-L-rhamnulose > L-fuculose 1-phosphate + Adenosine diphosphate + Hydrogen ion + L-Fuculose 1-phosphate + ADP PW_R002973