2.02012-05-31 14:06:22 -06002015-06-03 15:54:47 -0600ECMDB04144M2MDB000634L-RhamnuloseL-Rhamnulose is a breakdown product of L-rhamnose, which is ubiquitous and particularly abundant in some plants, such as buckthorn. Rhamnose is also one of the sugars regularly used to conduct the dual sugar permeability test. Rhamnose is fermented by some colonic bacteria into L-rhamnulose. Three bacterial (gut micrflora) enzymes are involved in Rhamnose degradation including rhaB (rhamulose kinase), rhaA (rhamnose isomerase), and rhaD (rhamnulose-1-phosphate aldolase). L-rhamnulose kinase catalyzes the transfer of the gamma-phosphate group from ATP to the 1-hydroxyl group of L-rhamnulose. E.coli are growing depending on L-rhamnose as a source of carbon and energy. (PMID: 40956)6-Deoxy-L-mannose6-Deoxy-L-sorbose6-Deoxy-L-xylo-hex-2-uloseL-MannomethyloseL-RhamnoseRhamnuloseC6H12O5164.1565164.068473494(3S,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-oneL-rhamnulose14807-05-7C[C@H](O)[C@@H](O)[C@H](O)C(=O)COInChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3/t3-,5+,6+/m0/s1QZNPNKJXABGCRC-OTWZMJIISA-NSolidCytosollogp-1.79logs0.37solubility3.88e+02 g/llogp-2.2pka_strongest_acidic10.47pka_strongest_basic-3.1iupac(3S,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-oneaverage_mass164.1565mono_mass164.068473494smilesC[C@H](O)[C@@H](O)[C@H](O)C(=O)COformulaC6H12O5inchiInChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3/t3-,5+,6+/m0/s1inchikeyQZNPNKJXABGCRC-OTWZMJIISA-Npolar_surface_area97.99refractivity36.02polarizability15.42rotatable_bond_count4acceptor_count5donor_count4physiological_charge0formal_charge0Fructose and mannose metabolismec00051Pentose and glucuronate interconversionsec00040Microbial metabolism in diverse environmentsec01120L-rhamnose degradation IRHAMCAT-PWYSpecdb::CMs11449Specdb::CMs39422Specdb::NmrOneD279198Specdb::NmrOneD279199Specdb::NmrOneD279200Specdb::NmrOneD279201Specdb::NmrOneD279202Specdb::NmrOneD279203Specdb::NmrOneD279204Specdb::NmrOneD279205Specdb::NmrOneD279206Specdb::NmrOneD279207Specdb::NmrOneD279208Specdb::NmrOneD279209Specdb::NmrOneD279210Specdb::NmrOneD279211Specdb::NmrOneD279212Specdb::NmrOneD279213Specdb::NmrOneD279214Specdb::NmrOneD279215Specdb::NmrOneD279216Specdb::NmrOneD279217Specdb::MsMs27497Specdb::MsMs27498Specdb::MsMs27499Specdb::MsMs34055Specdb::MsMs34056Specdb::MsMs34057HMDB10207439330388459C0086117897RHAMNULOSEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Boronat, A., Aguilar, J. (1979). "Rhamnose-induced propanediol oxidoreductase in Escherichia coli: purification, properties, and comparison with the fucose-induced enzyme." J Bacteriol 140:320-326.40956Petrich K, Ludwig P, Kuhn H, Schewe T: The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leucocytes by the 15-lipoxygenase product (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid: structure-activity relationship and mechanism of action. Biochem J. 1996 Mar 15;314 ( Pt 3):911-6.8615788Haviv F, Ratajczyk JD, DeNet RW, Martin YC, Dyer RD, Carter GW: Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J Med Chem. 1987 Feb;30(2):254-63.3806609L-rhamnose isomeraseP32170RHAA_ECOLIrhaAhttp://ecmdb.ca/proteins/P32170.xmlRhamnulokinaseP32171RHAB_ECOLIrhaBhttp://ecmdb.ca/proteins/P32171.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlalpha-L-Rhamnose + L-Rhamnose <> L-RhamnuloseR02437Adenosine triphosphate + L-Rhamnulose <> ADP + Hydrogen ion + L-Rhamnulose 1-phosphateR03014RHAMNULOKIN-RXNalpha-L-Rhamnose <> L-RhamnuloseR02437Adenosine triphosphate + L-Rhamnulose <> ADP + L-Rhamnulose 1-phosphateR03014L-rhamnose <> L-RhamnuloseRHAMNISOM-RXNL-Rhamnulose + Adenosine triphosphate > Hydrogen ion + L-Rhamnulose 1-phosphate + ADPRHAMNULOKIN-RXNalpha-L-Rhamnose > L-RhamnuloseAdenosine triphosphate + L-Rhamnulose > ADP + L-Rhamnulose 1-phosphate