2.0 2015-09-08 17:50:05 -0600 2015-09-14 16:46:34 -0600 ECMDB24211 M2MDB006328 L-rhamnulofuranose L-rhamnulose kinase (gene name: rhaB) is an enzyme that catalyses the chemical reaction L-rhamnulofuranose + ATP <=> L-rhamnulose 1-phosphate + ADP + H+ in E. coli (BioCyc). C6H12O5 164.157 164.068473486 2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol 2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol CC1OC(O)(CO)C(O)C1O InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3 CJJCPDZKQKUXSS-UHFFFAOYSA-N logp -1.79 ALOGPS logs 0.85 ALOGPS solubility 1.16e+03 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 10.29 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac 2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol ChemAxon average_mass 164.157 ChemAxon mono_mass 164.068473486 ChemAxon smiles CC1OC(O)(CO)C(O)C1O ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3 ChemAxon inchikey CJJCPDZKQKUXSS-UHFFFAOYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.82 ChemAxon polarizability 15.42 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 Specdb::CMs 1084332 Specdb::NmrOneD 291615 Specdb::NmrOneD 291616 Specdb::NmrOneD 291617 Specdb::NmrOneD 291618 Specdb::NmrOneD 291619 Specdb::NmrOneD 291620 Specdb::NmrOneD 291621 Specdb::NmrOneD 291622 Specdb::NmrOneD 291623 Specdb::NmrOneD 291624 Specdb::NmrOneD 291625 Specdb::NmrOneD 291626 Specdb::NmrOneD 291627 Specdb::NmrOneD 291628 Specdb::NmrOneD 291629 Specdb::NmrOneD 291630 Specdb::NmrOneD 291631 Specdb::NmrOneD 291632 Specdb::NmrOneD 291633 Specdb::NmrOneD 291634 Specdb::MsMs 23306 Specdb::MsMs 23307 Specdb::MsMs 23308 Specdb::MsMs 30104 Specdb::MsMs 30105 Specdb::MsMs 30106 Rhamnulokinase P32171 RHAB_ECOLI rhaB http://ecmdb.ca/proteins/P32171.xml L-rhamnulofuranose + Adenosine triphosphate + L-rhamnulofuranose > Adenosine diphosphate + Hydrogen ion + L-rhamnulose 1-phosphate + ADP + L-Rhamnulose 1-phosphate PW_R002970