2.0 2015-09-08 17:50:06 -0600 2015-09-14 16:46:35 -0600 ECMDB24212 M2MDB006329 β-L-fucopyranose beta-L-fucopyranose is an intermediate in fucose degradation pathway in E.coli. It is a substrate for the enzymes L-fucose mutarotase which catalyzes the reaction beta-L-fucopyranose -> alpha-L-fucopyranose (BioCyc compound: CPD-10329). C6H12O5 164.157 164.068473486 6-methyloxane-2,3,4,5-tetrol 6-methyloxane-2,3,4,5-tetrol CC1OC(O)C(O)C(O)C1O InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3 SHZGCJCMOBCMKK-UHFFFAOYSA-N logp -2.39 ALOGPS logs 0.70 ALOGPS solubility 8.27e+02 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 6-methyloxane-2,3,4,5-tetrol ChemAxon average_mass 164.157 ChemAxon mono_mass 164.068473486 ChemAxon smiles CC1OC(O)C(O)C(O)C1O ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3 ChemAxon inchikey SHZGCJCMOBCMKK-UHFFFAOYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.38 ChemAxon polarizability 15.34 ChemAxon rotatable_bond_count 0 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 50580 Specdb::CMs 61337 Specdb::CMs 116089 Specdb::CMs 122085 Specdb::CMs 122260 Specdb::CMs 123647 Specdb::CMs 151195 Specdb::CMs 827395 Specdb::CMs 827396 Specdb::NmrOneD 200367 Specdb::NmrOneD 200368 Specdb::NmrOneD 200369 Specdb::NmrOneD 200370 Specdb::NmrOneD 200371 Specdb::NmrOneD 200372 Specdb::NmrOneD 200373 Specdb::NmrOneD 200374 Specdb::NmrOneD 200375 Specdb::NmrOneD 200376 Specdb::NmrOneD 200377 Specdb::NmrOneD 200378 Specdb::NmrOneD 200379 Specdb::NmrOneD 200380 Specdb::NmrOneD 200381 Specdb::NmrOneD 200382 Specdb::NmrOneD 200383 Specdb::NmrOneD 200384 Specdb::NmrOneD 200385 Specdb::NmrOneD 200386 Specdb::MsMs 26252 Specdb::MsMs 26253 Specdb::MsMs 26254 Specdb::MsMs 32810 Specdb::MsMs 32811 Specdb::MsMs 32812 Specdb::MsMs 2702044 Specdb::MsMs 2702045 Specdb::MsMs 2702046 Specdb::MsMs 3006471 Specdb::MsMs 3006472 Specdb::MsMs 3006473 L-fucose mutarotase P0AEN8 FUCM_ECOLI fucU http://ecmdb.ca/proteins/P0AEN8.xml β-L-fucopyranose > alpha-L-Fucose PW_R002975