Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:43:20 UTC
Update Date2024-04-30 19:42:33 UTC
Metabolite IDMMDBc0029827
Metabolite Identification
Common NameDeoxythymidine diphosphate-L-rhamnose
DescriptionDeoxythymidine 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. 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 enzymes involved in dTDP-L-rhamnose synthesis are potential targets for the design of new therapeutic agents against bacteria. (PMID 10802738 , 12773151 )
Structure
Synonyms
ValueSource
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-beta-L-mannopyranosyl) esterChEBI
Thymidine diphosphate rhamnoseChEBI
Thymidine diphosphate-L-rhamnoseChEBI
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-b-L-mannopyranosyl) esterGenerator
Thymidine 5'-(trihydrogen diphosphate), p'-(6-deoxy-β-L-mannopyranosyl) esterGenerator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-b-L-mannopyranosyl) esterGenerator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-beta-L-mannopyranosyl) esterGenerator
Thymidine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-β-L-mannopyranosyl) esterGenerator
Thymidine diphosphoric acid rhamnoseGenerator
Thymidine diphosphoric acid-L-rhamnoseGenerator
Deoxythymidine diphosphoric acid-L-rhamnoseGenerator
dTDP-6-Deoxy-L-mannoseHMDB
dTDP-L-RhamnoseHMDB
Molecular FormulaC16H26N2O15P2
Average Mass548.3296
Monoisotopic Mass548.080841196
IUPAC Name{[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
Traditional Namedtdp-L-rhamnose
CAS Registry Number2147-59-3
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
InChI Identifier
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
InChI KeyZOSQFDVXNQFKBY-CZRCVJRHSA-N