1.0 2011-09-21 00:36:36 UTC 2015-07-21 06:57:55 UTC FDB023902 Deoxythymidine diphosphate-L-rhamnose Deoxythymidine diphosphate (dTDP)-l-rhamnose is the precursor of l-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram negative bacteria such as Salmonella enterica, Vibrio cholerae or Escherichia coli 075:K5, l-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and for colonization. In gram positive bacteria, such as streptococci, the capsule is a recognized virulence factor, for example, l-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, l-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle and heart tissues. In mycobacteria, l-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-l-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and in their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-l-rhamnose synthesis are potential targets for the design of new therapeutic agents. (PMID: 10802738, 12773151) [HMDB] dtdp-6-deoxy-l-mannose dTDP-L-rhamnose Thymidine 5'-(trihydrogen diate), p'-(6-deoxy-b-L-mannopyranosyl) ester Thymidine 5'-(trihydrogen diate), p'-(6-deoxy-beta-L-mannopyranosyl) ester Thymidine 5'-(trihydrogen diate), p'-(6-deoxy-β-L-mannopyranosyl) ester Thymidine 5'-(trihydrogen diic acid), p'-(6-deoxy-b-L-mannopyranosyl) ester Thymidine 5'-(trihydrogen diic acid), p'-(6-deoxy-beta-L-mannopyranosyl) ester Thymidine 5'-(trihydrogen diic acid), p'-(6-deoxy-β-L-mannopyranosyl) ester Thymidine diate rhamnose Thymidine diate-L-rhamnose Thymidine diic acid rhamnose Thymidine diic acid-L-rhamnose Thymidine diphosphate rhamnose Thymidine diphosphate-l-rhamnose C16H26N2O15P2 548.3296 548.080841196 {[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid dtdp-L-rhamnose 2147-59-3 C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,11-,12+,13+,15?/m0/s1 ZOSQFDVXNQFKBY-CZRCVJRHSA-N belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Pyrimidine nucleotide sugars Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleotides Pyrimidine nucleotide sugars Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Lactams Monoalkyl phosphates Monosaccharide phosphates Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Polyols Pyrimidine 2'-deoxyribonucleoside diphosphates Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides Alcohol Alkyl phosphate Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Lactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Pentose phosphate Phosphoric acid ester Polyol Pyrimidine Pyrimidine 2'-deoxyribonucleoside diphosphate Pyrimidine nucleotide sugar Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide dTDP-rhamnose Solid logp -1.09 ALOGPS logs -1.68 ALOGPS solubility 1.16e+01 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac {[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 548.3296 ChemAxon mono_mass 548.080841196 ChemAxon smiles C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C16H26N2O15P2 ChemAxon inchi InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,11-,12+,13+,15?/m0/s1 ChemAxon inchikey ZOSQFDVXNQFKBY-CZRCVJRHSA-N ChemAxon polar_surface_area 251.08 ChemAxon refractivity 107.76 ChemAxon polarizability 46.26 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 12 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16117 Specdb::CMs 39007 Specdb::MsMs 26108 Specdb::MsMs 26109 Specdb::MsMs 26110 Specdb::MsMs 32666 Specdb::MsMs 32667 Specdb::MsMs 32668 Specdb::NmrOneD 255248 Specdb::NmrOneD 255249 Specdb::NmrOneD 255250 Specdb::NmrOneD 255251 Specdb::NmrOneD 255252 Specdb::NmrOneD 255253 Specdb::NmrOneD 255254 Specdb::NmrOneD 255255 Specdb::NmrOneD 255256 Specdb::NmrOneD 255257 Specdb::NmrOneD 255258 Specdb::NmrOneD 255259 Specdb::NmrOneD 255260 Specdb::NmrOneD 255261 Specdb::NmrOneD 255262 Specdb::NmrOneD 255263 Specdb::NmrOneD 255264 Specdb::NmrOneD 255265 Specdb::NmrOneD 255266 Specdb::NmrOneD 255267 HMDB06354 35452 #<Reference:0x000055ce316b1ac0> #<Reference:0x000055ce316b1840>