2.02012-05-31 14:49:34 -06002015-06-03 17:20:11 -0600ECMDB20537M2MDB001344TDP-RhamnoseTDP-rhamnose is a member of the chemical class known as Mixed Pentose/Hexose Disaccharides. These are disaccharides containing both an hexose and a pentose. dTDP-rhamnose is an important precursor of cell wall polysaccharides and rhamnose-containing exopolysaccharides (EPS) in E. coli. (PMID 14973085)DTDP-6-Deoxy-L-mannoseDTDP-L-RhamnoseDTDP-RhamnoseTDP-rhamnoseC17H26N2O14P2544.3409544.0859265744-hydroxy-1-[(2S,4S,5S)-4-hydroxy-5-[2-({[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato]oxy}phosphinato)ethyl]oxolan-2-yl]-5-methyl-2-oxo-2,5-dihydro-1λ⁵-pyrimidine-1,5-bis(ylium)4-hydroxy-1-[(2S,4S,5S)-4-hydroxy-5-(2-{[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato]oxyphosphinato}ethyl)oxolan-2-yl]-5-methyl-2-oxo-5H-1λ⁵-pyrimidine-1,5-bis(ylium)[H][C@]1(O)C[C@]([H])(O[C@@]1([H])CCP([O-])(=O)OP([O-])(=O)O[C@@]1([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)[N+]1=C[C+](C)C(O)=NC1=OInChI=1S/C17H26N2O14P2/c1-7-6-19(17(25)18-15(7)24)11-5-9(20)10(31-11)3-4-34(26,27)33-35(28,29)32-16-14(23)13(22)12(21)8(2)30-16/h6,8-14,16,20-23H,3-5H2,1-2H3,(H-2,18,24,25,26,27,28,29)/t8-,9-,10-,11-,12+,13+,14+,16+/m0/s1NQGLMWQXKRELIQ-AYDVIBIJSA-NCytoplasmPeriplasmlogp0.32logs-1.84solubility9.33e+00 g/llogp-7.3pka_strongest_acidic-6.8pka_strongest_basic-3.3iupac4-hydroxy-1-[(2S,4S,5S)-4-hydroxy-5-[2-({[(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl phosphonato]oxy}phosphinato)ethyl]oxolan-2-yl]-5-methyl-2-oxo-2,5-dihydro-1λ⁵-pyrimidine-1,5-bis(ylium)average_mass544.3409mono_mass544.085926574smiles[H][C@]1(O)C[C@]([H])(O[C@@]1([H])CCP([O-])(=O)OP([O-])(=O)O[C@@]1([H])O[C@@]([H])(C)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)[N+]1=C[C+](C)C(O)=NC1=OformulaC17H26N2O14P2inchiInChI=1S/C17H26N2O14P2/c1-7-6-19(17(25)18-15(7)24)11-5-9(20)10(31-11)3-4-34(26,27)33-35(28,29)32-16-14(23)13(22)12(21)8(2)30-16/h6,8-14,16,20-23H,3-5H2,1-2H3,(H-2,18,24,25,26,27,28,29)/t8-,9-,10-,11-,12+,13+,14+,16+/m0/s1inchikeyNQGLMWQXKRELIQ-AYDVIBIJSA-Npolar_surface_area250.77refractivity108.28polarizability47.31rotatable_bond_count8acceptor_count13donor_count5physiological_charge-1formal_charge0dTDP-L-rhamnose biosynthesis IDTDPRHAMSYN-PWYSpecdb::NmrOneD285309Specdb::NmrOneD285310Specdb::NmrOneD285311Specdb::NmrOneD285312Specdb::NmrOneD285313Specdb::NmrOneD285314Specdb::NmrOneD285315Specdb::NmrOneD285316Specdb::NmrOneD285317Specdb::NmrOneD285318Specdb::NmrOneD285319Specdb::NmrOneD285320Specdb::NmrOneD285321Specdb::NmrOneD285322Specdb::NmrOneD285323Specdb::NmrOneD285324Specdb::NmrOneD285325Specdb::NmrOneD285326Specdb::NmrOneD285327Specdb::NmrOneD285328Specdb::MsMs1235482Specdb::MsMs1235483Specdb::MsMs1235484Specdb::MsMs1350958Specdb::MsMs1350959Specdb::MsMs135096025200574DTDP-RHAMNOSEKeseler, 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-D590.21097882Boels, I. C., Beerthuyzen, M. M., Kosters, M. H., Van Kaauwen, M. P., Kleerebezem, M., De Vos, W. M. (2004). "Identification and functional characterization of the Lactococcus lactis rfb operon, required for dTDP-rhamnose Biosynthesis." J Bacteriol 186:1239-1248.14973085dTDP-4-dehydrorhamnose reductaseP37760RMLD_ECOLIrfbDhttp://ecmdb.ca/proteins/P37760.xmldTDP-4-dehydro-beta-L-rhamnose + NADH + Hydrogen ion > NADP + TDP-RhamnosePW_R006147