2.0 2012-10-10 12:15:09 -0600 2015-06-03 17:25:52 -0600 ECMDB23078 M2MDB003468 beta-L-Rhamnose beta-L-Rhamnose is an anomer of alpha-L-rhamnose. It is a substrate of the E. coli enzyme L-rhamnose mutarotase. An anomer is a special type of epimer. It is one of two stereoisomers of a cyclic saccharide that differs only in its configuration at the hemiacetal or hemiketal carbon, also called the anomeric carbon. b-6-Deoxy-L-mannose b-L-Mannomethylose b-L-Rhamnose Beta-6-Deoxy-L-mannose Beta-L-Mannomethylose L-Rhamnose β-6-Deoxy-L-mannose β-L-Mannomethylose β-L-Rhamnose C6H12O5 164.1565 164.068473494 (2S,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol β-L-rhamnose 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-YJRYQGEOSA-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 (2S,3R,4R,5R,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-YJRYQGEOSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.38 ChemAxon polarizability 15.32 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 1084872 Specdb::EiMs 3466 Specdb::NmrOneD 311451 Specdb::NmrOneD 311452 Specdb::NmrOneD 311453 Specdb::NmrOneD 311454 Specdb::NmrOneD 311455 Specdb::NmrOneD 311456 Specdb::NmrOneD 311457 Specdb::NmrOneD 311458 Specdb::NmrOneD 311459 Specdb::NmrOneD 311460 Specdb::NmrOneD 311461 Specdb::NmrOneD 311462 Specdb::NmrOneD 311463 Specdb::NmrOneD 311464 Specdb::NmrOneD 311465 Specdb::NmrOneD 311466 Specdb::NmrOneD 311467 Specdb::NmrOneD 311468 Specdb::NmrOneD 311469 Specdb::NmrOneD 311470 Specdb::MsMs 27062 Specdb::MsMs 27063 Specdb::MsMs 27064 Specdb::MsMs 33620 Specdb::MsMs 33621 Specdb::MsMs 33622 439730 C02338 27586 RM4 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 alpha-L-Rhamnose > beta-L-Rhamnose alpha-L-Rhamnose <> beta-L-Rhamnose R10819 beta-L-Rhamnose > keto-L-rhamnulose + keto-L-rhamnulose PW_R002968