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Chemical Compound Review

CTK8H6049     [hydroxy-[[3-hydroxy-5-(5- methyl-2,4-dioxo...

Synonyms: AC1L19SK
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Disease relevance of dTDP-alpha-L-rhamnose


High impact information on dTDP-alpha-L-rhamnose


Chemical compound and disease context of dTDP-alpha-L-rhamnose


Biological context of dTDP-alpha-L-rhamnose

  • A reporter plasmid to detect genes encoding enzymes of the dTDP-rhamnose pathway is described [2].
  • The nucleotide sequence of the proximal half of the rfb region of Shigella flexneri has been determined, and the genes encoding enzymes involved in the biosynthesis of dTDP-rhamnose have been identified [2].
  • The same phenotype was seen in a mutant obtained by allelic exchange in rmlD, another ORF in this dTDP-rhamnose biosynthetic cluster [14].
  • Comparison of the four dTDP-L-rhamnose pathway genes (rml genes) of CPS types 1, 2, 6B, 18C, 19F, 19A, and 23F shows that they have the same gene order and are highly conserved [15].
  • The S88 locus contained a four-gene operon for the biosynthesis of dTDP-L-rhamnose, an essential precursor for the sphingans [16].

Anatomical context of dTDP-alpha-L-rhamnose


Associations of dTDP-alpha-L-rhamnose with other chemical compounds


Gene context of dTDP-alpha-L-rhamnose

  • In addition, genes rfbA, -B, -C, and -D were identified in the genome of A. ferrooxidans, suggesting that it can also synthesize the EPS precursor dTDP-rhamnose [22].
  • We conclude that the absence of a homolog for rfbC precludes the existence of a functional dTDP-rhamnose biosynthesis pathway in the gonococcal strains examined and that these genes are only maintained in N. gonorrhoeae either because of the presence of the galE gene or because of another as yet unrecognized function [23].
  • Eight genes were identified in the rfb fragment: the rfbB-CAD cluster which encodes dTDP-rhamnose synthesis, rfbX which encodes a hydrophobic protein involved in assembly of the O antigen, rfc which encodes the O antigen polymerase, and two sugar transferase genes [24].
  • A nonpolar mutation was made in the oac2 gene of Azorhizobium caulinodans. oac2 is an ortholog of the Salmonella typhimurium rfbD gene that encodes a dTDP-L-rhamnose synthase [18].
  • We had isolated three genes (rmlA, rmlB, and rmlC) involved in dTDP-rhamnose synthesis in Streptococcus mutans and found that three genes were insufficient for dTDP-rhamnose synthesis (Y. Tsukioka, Y. Yamashita, T. Oho, Y. Nakano, and T. Koga, J. Bacteriol. 179:1126-1134, 1997) [25].

Analytical, diagnostic and therapeutic context of dTDP-alpha-L-rhamnose

  • Genetic and sequence analyses of one such transport-defective mutant revealed that the transposon insertion occurred in an open reading frame (ORF) with homology to rmlC, a dTDP-rhamnose biosynthetic gene [14].
  • Overexpression, purification, crystallization and preliminary structural study of dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD), the fourth enzyme of the dTDP-L-rhamnose synthesis pathway, from Salmonella enterica serovar Typhimurium [26].
  • From the reaction with 20 ml volume, approximately 180 mg of dTDP-L-rhamnose was obtained in an overall yield of 60% after two-step purification, that is, anion exchange chromatography and gel filtration for desalting [27].
  • Furthermore, an HPLC technique is presented for determining the net activity of dTDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase and NADPH:dTDP-6-deoxy-L-lyxo-4-hexulose-4-reductase, based on separation of dTDP-6-deoxy-D-xylo-4-hexulose and dTDP-L-rhamnose [28].


  1. Characterization of dTDP-4-dehydrorhamnose 3,5-epimerase and dTDP-4-dehydrorhamnose reductase, required for dTDP-L-rhamnose biosynthesis in Salmonella enterica serovar Typhimurium LT2. Graninger, M., Nidetzky, B., Heinrichs, D.E., Whitfield, C., Messner, P. J. Biol. Chem. (1999) [Pubmed]
  2. Characterization of the dTDP-rhamnose biosynthetic genes encoded in the rfb locus of Shigella flexneri. Macpherson, D.F., Manning, P.A., Morona, R. Mol. Microbiol. (1994) [Pubmed]
  3. Molecular organization of the genes required for the synthesis of type 1 capsular polysaccharide of Streptococcus pneumoniae: formation of binary encapsulated pneumococci and identification of cryptic dTDP-rhamnose biosynthesis genes. Muñoz, R., Mollerach, M., López, R., García, E. Mol. Microbiol. (1997) [Pubmed]
  4. Genetic organization and sequence of the rfb gene cluster of Yersinia enterocolitica serotype O:3: similarities to the dTDP-L-rhamnose biosynthesis pathway of Salmonella and to the bacterial polysaccharide transport systems. Zhang, L., al-Hendy, A., Toivanen, P., Skurnik, M. Mol. Microbiol. (1993) [Pubmed]
  5. Recombination between gtfB and gtfC is required for survival of a dTDP-rhamnose synthesis-deficient mutant of Streptococcus mutans in the presence of sucrose. Yamashita, Y., Tomihisa, K., Nakano, Y., Shimazaki, Y., Oho, T., Koga, T. Infect. Immun. (1999) [Pubmed]
  6. Biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-galactose in Aneurinibacillus thermoaerophilus L420-91T. Pfoestl, A., Hofinger, A., Kosma, P., Messner, P. J. Biol. Chem. (2003) [Pubmed]
  7. Thymidine diphosphate-6-deoxy-L-lyxo-4-hexulose reductase synthesizing dTDP-6-deoxy-L-talose from Actinobacillus actinomycetemcomitans. Nakano, Y., Suzuki, N., Yoshida, Y., Nezu, T., Yamashita, Y., Koga, T. J. Biol. Chem. (2000) [Pubmed]
  8. Cloning and functional characterization of the Pseudomonas aeruginosa rhlC gene that encodes rhamnosyltransferase 2, an enzyme responsible for di-rhamnolipid biosynthesis. Rahim, R., Ochsner, U.A., Olvera, C., Graninger, M., Messner, P., Lam, J.S., Soberón-Chávez, G. Mol. Microbiol. (2001) [Pubmed]
  9. Characterization of the locus encoding the Streptococcus pneumoniae type 19F capsular polysaccharide biosynthetic pathway. Morona, J.K., Morona, R., Paton, J.C. Mol. Microbiol. (1997) [Pubmed]
  10. Genetic organization of the O7-specific lipopolysaccharide biosynthesis cluster of Escherichia coli VW187 (O7:K1). Marolda, C.L., Feldman, M.F., Valvano, M.A. Microbiology (Reading, Engl.) (1999) [Pubmed]
  11. Purification, characterization and HPLC assay of Salmonella glucose-1-phosphate thymidylyl-transferase from the cloned rfbA gene. Lindquist, L., Kaiser, R., Reeves, P.R., Lindberg, A.A. Eur. J. Biochem. (1993) [Pubmed]
  12. A structural perspective on the enzymes that convert dTDP-d-glucose into dTDP-l-rhamnose. Dong, C., Beis, K., Giraud, M.F., Blankenfeldt, W., Allard, S., Major, L.L., Kerr, I.D., Whitfield, C., Naismith, J.H. Biochem. Soc. Trans. (2003) [Pubmed]
  13. Variation on a theme of SDR. dTDP-6-deoxy-L- lyxo-4-hexulose reductase (RmlD) shows a new Mg2+-dependent dimerization mode. Blankenfeldt, W., Kerr, I.D., Giraud, M.F., McMiken, H.J., Leonard, G., Whitfield, C., Messner, P., Graninger, M., Naismith, J.H. Structure (Camb.) (2002) [Pubmed]
  14. Novel role of the lipopolysaccharide O1 side chain in ferric siderophore transport and virulence of Vibrio anguillarum. Welch, T.J., Crosa, J.H. Infect. Immun. (2005) [Pubmed]
  15. Molecular characterization of Streptococcus pneumoniae type 4, 6B, 8, and 18C capsular polysaccharide gene clusters. Jiang, S.M., Wang, L., Reeves, P.R. Infect. Immun. (2001) [Pubmed]
  16. Linkage of genes essential for synthesis of a polysaccharide capsule in Sphingomonas strain S88. Yamazaki, M., Thorne, L., Mikolajczak, M., Armentrout, R.W., Pollock, T.J. J. Bacteriol. (1996) [Pubmed]
  17. Mycobacterium tuberculosis RmlC epimerase (Rv3465): a promising drug-target structure in the rhamnose pathway. Kantardjieff, K.A., Kim, C.Y., Naranjo, C., Waldo, G.S., Lekin, T., Segelke, B.W., Zemla, A., Park, M.S., Terwilliger, T.C., Rupp, B. Acta Crystallogr. D Biol. Crystallogr. (2004) [Pubmed]
  18. Knockout of an azorhizobial dTDP-L-rhamnose synthase affects lipopolysaccharide and extracellular polysaccharide production and disables symbiosis with Sesbania rostrata. Gao, M., D'Haeze, W., De Rycke, R., Wolucka, B., Holsters, M. Mol. Plant Microbe Interact. (2001) [Pubmed]
  19. S-layer glycan-specific loci on the chromosome of Geobacillus stearothermophilus NRS 2004/3a and dTDP-L-rhamnose biosynthesis potential of G. stearothermophilus strains. Novotny, R., Schäffer, C., Strauss, J., Messner, P. Microbiology (Reading, Engl.) (2004) [Pubmed]
  20. The purification, crystallization and preliminary structural characterization of glucose-1-phosphate thymidylyltransferase (RmlA), the first enzyme of the dTDP-L-rhamnose synthesis pathway from Pseudomonas aeruginosa. Blankenfeldt, W., Giraud, M.F., Leonard, G., Rahim, R., Creuzenet, C., Lam, J.S., Naismith, J.H. Acta Crystallogr. D Biol. Crystallogr. (2000) [Pubmed]
  21. Metabolic engineering of the heterologous production of clorobiocin derivatives and elloramycin in Streptomyces coelicolor M512. Freitag, A., M??ndez, C., Salas, J.A., Kammerer, B., Li, S.M., Heide, L. Metab. Eng. (2006) [Pubmed]
  22. Identification of a gene cluster for the formation of extracellular polysaccharide precursors in the chemolithoautotroph Acidithiobacillus ferrooxidans. Barreto, M., Jedlicki, E., Holmes, D.S. Appl. Environ. Microbiol. (2005) [Pubmed]
  23. The identification of cryptic rhamnose biosynthesis genes in Neisseria gonorrhoeae and their relationship to lipopolysaccharide biosynthesis. Robertson, B.D., Frosch, M., van Putten, J.P. J. Bacteriol. (1994) [Pubmed]
  24. Function of the rfb gene cluster and the rfe gene in the synthesis of O antigen by Shigella dysenteriae 1. Klena, J.D., Schnaitman, C.A. Mol. Microbiol. (1993) [Pubmed]
  25. Identification of a fourth gene involved in dTDP-rhamnose synthesis in Streptococcus mutans. Tsukioka, Y., Yamashita, Y., Nakano, Y., Oho, T., Koga, T. J. Bacteriol. (1997) [Pubmed]
  26. Overexpression, purification, crystallization and preliminary structural study of dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD), the fourth enzyme of the dTDP-L-rhamnose synthesis pathway, from Salmonella enterica serovar Typhimurium. Giraud, M.F., McMiken, H.J., Leonard, G.A., Messner, P., Whitfield, C., Naismith, J.H. Acta Crystallogr. D Biol. Crystallogr. (1999) [Pubmed]
  27. Preparative synthesis of dTDP-L-rhamnose through combined enzymatic pathways. Kang, Y.B., Yang, Y.H., Lee, K.W., Lee, S.G., Sohng, J.K., Lee, H.C., Liou, K., Kim, B.G. Biotechnol. Bioeng. (2006) [Pubmed]
  28. Enzymatic synthesis and isolation of thymidine diphosphate-6-deoxy-D-xylo-4-hexulose and thymidine diphosphate-L-rhamnose. Production using cloned gene products and separation by HPLC. Marumo, K., Lindqvist, L., Verma, N., Weintraub, A., Reeves, P.R., Lindberg, A.A. Eur. J. Biochem. (1992) [Pubmed]
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