2.0 2012-05-31 13:01:34 -0600 2015-09-13 12:56:09 -0600 ECMDB00849 M2MDB000192 alpha-L-Rhamnose Rhamnose is a methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides. 6-Deoxy-L(+)-mannose 6-Deoxy-L-Mannopyranose 6-Deoxy-L-mannose 6-Deoxy-Mannose 6-Deoxyhexopyranose 6-Deoxyhexose 6-Deoxymannose a-L-Rhamnose Isodulcit Isodulcitol L(+)-Rhamnose L(+)-Rhamnose monohydrate L(+)-Rhamnose monohydric acid L-(+)-Rhamnose L-(+)-Rhamnose 1-hydrate L-(+)-Rhamnose 1-hydric acid L-(+)-Rhamnose Hydrate = 6-Deoxy-L-mannose Monohydrate L-(+)-Rhamnose Hydric acid = 6-Deoxy-L-mannose Monohydrate L-(+)-Rhamnose hydric acid = 6-deoxy-L-mannose monohydric acid L-(+)-Rhamnose monohydrate L-(+)-Rhamnose monohydric acid L-Mannomethylose L-Rhamnopyranose L-Rhamnose L-Rhamnose for biochemistry L-Rhamnose Monohydrate L-Rhamnose Monohydric acid Locaose Mono(6-deoxy-b-L-mannopyranosyl) ester Mono(6-deoxy-beta-L-mannopyranosyl) ester mono(6-Deoxy-β-L-mannopyranosyl) ester P-(6-Deoxy-b-L-mannopyranosyl) ester P-(6-Deoxy-beta-L-mannopyranosyl) ester P-(6-Deoxy-β-L-mannopyranosyl) ester Rhamnopyranose Rhamnose Rhamnosemonohydrate Rhamnosemonohydric acid UDP-Rhamnose Uridine 5-pyrophosphate Uridine 5-pyrophosphoric acid Uridine diphosphate rhamnose Uridine diphosphoric acid rhamnose α-L-Rhamnose C6H12O5 164.1565 164.068473494 (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol α-L-rhamnopyranose 3615-41-6 [H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O 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-HGVZOGFYSA-N Solid Cytosol Extra-organism Periplasm logp -2.39 ALOGPS logs 0.70 ALOGPS solubility 8.27e+02 g/l ALOGPS melting_point 122 oC logp -1.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol ChemAxon average_mass 164.1565 ChemAxon mono_mass 164.068473494 ChemAxon smiles [H][C@@]1(C)O[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O 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-HGVZOGFYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.38 ChemAxon polarizability 15.26 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 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 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic Specdb::CMs 1084462 Specdb::EiMs 4571 Specdb::NmrOneD 338688 Specdb::NmrOneD 338689 Specdb::NmrOneD 338690 Specdb::NmrOneD 338691 Specdb::NmrOneD 338692 Specdb::NmrOneD 338693 Specdb::NmrOneD 338694 Specdb::NmrOneD 338695 Specdb::NmrOneD 338696 Specdb::NmrOneD 338697 Specdb::NmrOneD 338698 Specdb::NmrOneD 338699 Specdb::NmrOneD 338700 Specdb::NmrOneD 338701 Specdb::NmrOneD 338702 Specdb::NmrOneD 338703 Specdb::NmrOneD 338704 Specdb::NmrOneD 338705 Specdb::NmrOneD 338706 Specdb::NmrOneD 338707 Specdb::MsMs 28019 Specdb::MsMs 28020 Specdb::MsMs 28021 Specdb::MsMs 34577 Specdb::MsMs 34578 Specdb::MsMs 34579 HMDB00849 840 23642 C02476 16055 RHAMNOSE RAM Rhamnose Keseler, I. 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"Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Cambronero Sanchez, Miguel; Garcia Ruiz, Pedro Antonio. Preparation of high-purity L-rhamnose from rhamnoglucosides. Span. (1997), 7 pp. http://hmdb.ca/system/metabolites/msds/000/000/767/original/HMDB00849.pdf?1358462811 L-rhamnose isomerase P32170 RHAA_ECOLI rhaA http://ecmdb.ca/proteins/P32170.xml L-rhamnose mutarotase P32156 RHAM_ECOLI rhaM http://ecmdb.ca/proteins/P32156.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml L-rhamnose-proton symporter P27125 RHAT_ECOLI rhaT http://ecmdb.ca/proteins/P27125.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml alpha-L-Rhamnose + L-Rhamnose <> L-Rhamnulose R02437 alpha-L-Rhamnose <> L-Rhamnulose R02437 alpha-L-Rhamnose &beta;-L-rhamnose RXN0-5306 alpha-L-Rhamnose > L-Rhamnulose alpha-L-Rhamnose > beta-L-Rhamnose alpha-L-Rhamnose <> beta-L-Rhamnose R10819