2.0 2012-05-31 14:31:00 -0600 2015-09-17 15:42:01 -0600 ECMDB20166 M2MDB001013 L-Rhamnulose 1-phosphate L-rhamnulose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 6-Deoxy-1-O-phosphono-L-sorbose 6-Deoxy-L-sorbose 1-(dihydrogen phosphate) 6-Deoxy-L-sorbose 1-(dihydrogen phosphoric acid) 6-Deoxy-L-sorbose 1-phosphate 6-Deoxy-L-sorbose 1-phosphoric acid L-Rhamnulose 1-phosphoric acid L-Rhamnulose-1P Rhamnulose 1-phosphate Rhamnulose 1-phosphoric acid Rhamnulose-1-P Rhamnulose-1-phosphate Rhamnulose-1-phosphoric acid C9H19O5P 238.22 238.09701071 {[(3S,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid L-rhamnulose 1-phosphate 444-09-7 CC(O)C(O)C(O)C(=C)COP(C)(O)=C InChI=1S/C9H19O5P/c1-6(5-14-15(3,4)13)8(11)9(12)7(2)10/h7-13H,1,3,5H2,2,4H3 QRXAIBTYLQNPRQ-UHFFFAOYSA-N 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 {[(3S,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid ChemAxon average_mass 238.22 ChemAxon mono_mass 238.09701071 ChemAxon smiles CC(O)C(O)C(O)C(=C)COP(C)(O)=C ChemAxon formula C9H19O5P ChemAxon inchi InChI=1S/C9H19O5P/c1-6(5-14-15(3,4)13)8(11)9(12)7(2)10/h7-13H,1,3,5H2,2,4H3 ChemAxon inchikey QRXAIBTYLQNPRQ-UHFFFAOYSA-N ChemAxon polar_surface_area 144.52 ChemAxon refractivity 46.89 ChemAxon polarizability 20.08 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 Pentose and glucuronate interconversions ec00040 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 L-rhamnose degradation I RHAMCAT-PWY Specdb::MsMs 28457 Specdb::MsMs 28458 Specdb::MsMs 28459 Specdb::MsMs 35015 Specdb::MsMs 35016 Specdb::MsMs 35017 439413 388527 C01131 17892 RHAMNULOSE-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 Rhamnulose-1-phosphate aldolase P32169 RHAD_ECOLI rhaD http://ecmdb.ca/proteins/P32169.xml Rhamnulokinase P32171 RHAB_ECOLI rhaB http://ecmdb.ca/proteins/P32171.xml L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde R02263 RHAMNULPALDOL-RXN Adenosine triphosphate + L-Rhamnulose <> ADP + Hydrogen ion + L-Rhamnulose 1-phosphate R03014 RHAMNULOKIN-RXN L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde R02263 Adenosine triphosphate + L-Rhamnulose <> ADP + L-Rhamnulose 1-phosphate R03014 L-Rhamnulose + Adenosine triphosphate > Hydrogen ion + L-Rhamnulose 1-phosphate + ADP RHAMNULOKIN-RXN Adenosine triphosphate + L-Rhamnulose > ADP + L-Rhamnulose 1-phosphate L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde L-rhamnulofuranose + Adenosine triphosphate + L-rhamnulofuranose > Adenosine diphosphate + Hydrogen ion + L-rhamnulose 1-phosphate + ADP + L-Rhamnulose 1-phosphate PW_R002970 L-rhamnulose 1-phosphate + L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde PW_R002971