2.0 2012-05-31 14:36:06 -0600 2015-06-03 17:19:40 -0600 ECMDB20264 M2MDB001107 alpha-L-Fucose Fucose is a hexose sugar with the chemical formula C6H12O5. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. α-L-fucopyranose (-)-fucose (-)-L-fucose 6-Deoxy-b-galactose 6-Deoxy-beta-galactose 6-Deoxy-D-galactopyranose 6-Deoxy-delta-galactopyranose 6-Deoxy-L-b-galactose 6-Deoxy-L-beta-galactose 6-Deoxy-L-galactopyranose 6-Deoxy-L-galactose 6-Deoxy-L-β-galactose 6-Deoxy-β-galactose 6-Deoxy-δ-galactopyranose 6-Desoxygalactose 6-Methyloxane-2,3,4,5-tetrol 6-Methyltetrahydropyran-2,3,4,5-tetraol a-L-Fucopyranose a-L-Fucose Alpha-L-Fucopyranose D-Threo-aldose F2252_SIGMA FUC Fucopyranose, L- (7CI) Fucose Isodulcit L-Fucose α-L-Fucopyranose α-L-Fucose C6H12O5 164.1565 164.068473494 (2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol α-L-fucose 2438-80-4 C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1 SHZGCJCMOBCMKK-SXUWKVJYSA-N Solid Cytoplasm Periplasm logp -2.39 ALOGPS logs 0.70 ALOGPS solubility 8.27e+02 g/l ALOGPS melting_point 140 oC logp -1.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol ChemAxon average_mass 164.1565 ChemAxon mono_mass 164.068473494 ChemAxon smiles C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1 ChemAxon inchikey SHZGCJCMOBCMKK-SXUWKVJYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.38 ChemAxon polarizability 15.21 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Amino sugar and nucleotide sugar metabolism ec00520 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 103900 Specdb::CMs 103901 Specdb::CMs 103902 Specdb::CMs 103903 Specdb::CMs 134163 Specdb::CMs 141897 Specdb::CMs 1052689 Specdb::CMs 1052691 Specdb::CMs 1052693 Specdb::CMs 1052694 Specdb::CMs 1052696 Specdb::CMs 1052698 Specdb::CMs 1052700 Specdb::CMs 1052702 Specdb::CMs 1052704 Specdb::CMs 1052706 Specdb::CMs 1052707 Specdb::CMs 1052709 Specdb::CMs 1052711 Specdb::CMs 1052713 Specdb::CMs 1052714 Specdb::CMs 1052716 Specdb::CMs 1052718 Specdb::CMs 1052720 Specdb::CMs 1052722 Specdb::NmrOneD 5279 Specdb::NmrOneD 5280 Specdb::NmrOneD 5992 Specdb::NmrOneD 5993 Specdb::NmrOneD 5994 Specdb::NmrOneD 5995 Specdb::NmrOneD 5996 Specdb::NmrOneD 5997 Specdb::NmrOneD 5998 Specdb::NmrOneD 5999 Specdb::NmrOneD 6000 Specdb::NmrOneD 6001 Specdb::NmrOneD 6002 Specdb::NmrOneD 6003 Specdb::NmrOneD 6004 Specdb::NmrOneD 6005 Specdb::NmrOneD 6006 Specdb::NmrOneD 6007 Specdb::NmrOneD 6008 Specdb::NmrOneD 6009 Specdb::NmrOneD 6010 Specdb::NmrOneD 6011 Specdb::MsMs 28583 Specdb::MsMs 28584 Specdb::MsMs 28585 Specdb::MsMs 35141 Specdb::MsMs 35142 Specdb::MsMs 35143 Specdb::MsMs 1480167 Specdb::MsMs 1480168 Specdb::MsMs 1480169 Specdb::MsMs 2677449 Specdb::MsMs 2677450 Specdb::MsMs 2677451 Specdb::MsMs 3028751 Specdb::MsMs 3028752 Specdb::MsMs 3028753 Specdb::NmrTwoD 2087 Specdb::NmrTwoD 2088 17106 817 C01019 18287 CPD-10329 FUC 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 L-fucose mutarotase P0AEN8 FUCM_ECOLI fucU http://ecmdb.ca/proteins/P0AEN8.xml L-fucose isomerase P69922 FUCI_ECOLI fucI http://ecmdb.ca/proteins/P69922.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml alpha-L-Fucose > beta-L-fucose alpha-L-Fucose > keto-L-rhamnulose PW_R002974 β-L-fucopyranose > alpha-L-Fucose PW_R002975