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Chemical Compound Review:

D-Rhamnose (2S,3S,4S,5S,6R)-6- methyloxane-2,3,4,5-tetrol

Synonyms: alpha-D-Rha, alpha-D-Rhap, SureCN1192464, CHEBI:63152, ZINC01532676, ...

Ramm, M. et al., Hwang, B.Y. et al., Reuhs, B.L. et al., Vinogradov, E.V. et al., Molinaro, A. et al., et al.

Ramm, Lobe, Hamburger,

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Disease relevance of C01684

Synthesis of the A-band polysaccharide sugar D-rhamnose requires Rmd and WbpW: identification of multiple AlgA homologues, WbpW and ORF488, in Pseudomonas aeruginosa [1].
A novel O-specific polysaccharide containing 3-acetamido-3-deoxy-alpha-D-fucose (Fuc3NAc) and D-rhamnose was isolated from the phenol-soluble lipopolysaccharide fraction of the plant associated bacterium Xanthomonas campestris strain 8004 [2].

High impact information on C01684

WecE also showed a similar activity for TDP-4-keto 6-deoxy-D-mannose (TDP-D-Man4O), but no activity for GDP-4-keto-6-deoxy-D-mannose (GDP-D-Man4O), suggesting that the nucleotide moiety would become a key determinant to the substrate specificity of amine acceptor for the activity of the SAT [3].
This rhamnan O antigen, which is absent from noninduced cells, has the same primary sequence as the A-band O antigen of Pseudomonas aeruginosa, except that it is composed of L-rhamnose rather than the D-rhamnose characteristic of the latter [4].
Surprisingly, inactivation of wzx also led to a marked delay in production of the ATP-binding cassette-transporter-dependent, D-rhamnose homopolymer, A-band LPS [5].
A-band, a D-rhamnose-containing common lipopolysaccharide antigen isolated from Pseudomonas aeruginosa AK1401, was found to be a receptor for bacteriophage A7 [6].
Amino acid sequence comparisons suggest that ata12 and ataPKS1 could be implicated in the biosynthesis of the d-rhamnose and alpha-p-coumaric acid moieties of A201A [7].

Chemical compound and disease context of C01684

It involves purification of LPS from Pseudomonas syringae pv. phaseolicola by phenol extraction and hydrophobic interaction chromatography (HIC), followed by mild hydrolysis and cleavage of the O-antigen into D-fucose and D-rhamnose [8].

Associations of C01684 with other chemical compounds

The O-specific polysaccharide, liberated from LPS by mild acetic acid hydrolysis, had a branched pentasaccharide repeating-unit composed of D-glucose, L-rhamnose, D-rhamnose, and 3-O-methyl-L-rhamnose in approximate molar ratios of 2:1:1:1 [9].

Analytical, diagnostic and therapeutic context of C01684

The monosaccharides were separated by column chromatography, and D-rhamnose recovered after filtration over Sephadex-LH 20 [8].

References

Synthesis of the A-band polysaccharide sugar D-rhamnose requires Rmd and WbpW: identification of multiple AlgA homologues, WbpW and ORF488, in Pseudomonas aeruginosa. Rocchetta, H.L., Pacan, J.C., Lam, J.S. Mol. Microbiol. (1998) [Pubmed]
Structural elucidation of the O-chain of the lipopolysaccharide from Xanthomonas campestris strain 8004. Molinaro, A., Silipo, A., Lanzetta, R., Newman, M.A., Dow, J.M., Parrilli, M. Carbohydr. Res. (2003) [Pubmed]
Characterization and investigation of substrate specificity of the sugar aminotransferase WecE from E. coli K12. Hwang, B.Y., Lee, H.J., Yang, Y.H., Joo, H.S., Kim, B.G. Chem. Biol. (2004) [Pubmed]
Structural characterization of a flavonoid-inducible Pseudomonas aeruginosa A-band-like O antigen of Rhizobium sp. strain NGR234, required for the formation of nitrogen-fixing nodules. Reuhs, B.L., Relić, B., Forsberg, L.S., Marie, C., Ojanen-Reuhs, T., Stephens, S.B., Wong, C.H., Jabbouri, S., Broughton, W.J. J. Bacteriol. (2005) [Pubmed]
Effect of wzx (rfbX) mutations on A-band and B-band lipopolysaccharide biosynthesis in Pseudomonas aeruginosa O5. Burrows, L.L., Lam, J.S. J. Bacteriol. (1999) [Pubmed]
Common antigen lipopolysaccharide from Pseudomonas aeruginosa AK1401 as a receptor for bacteriophage A7. Rivera, M., Chivers, T.R., Lam, J.S., McGroarty, E.J. J. Bacteriol. (1992) [Pubmed]
Identification of a set of genes involved in the biosynthesis of the aminonucleoside moiety of antibiotic A201A from Streptomyces capreolus. Saugar, I., Sanz, E., Rubio, M.A., Espinosa, J.C., Jiménez, A. Eur. J. Biochem. (2002) [Pubmed]
A simple method for preparation of D-rhamnose. Ramm, M., Lobe, M., Hamburger, M. Carbohydr. Res. (2003) [Pubmed]
The structure of the O-specific polysaccharide from Thiobacillus ferrooxidans IFO 14262. Vinogradov, E.V., Campos-Portuguez, S., Yokota, A., Mayer, H. Carbohydr. Res. (1994) [Pubmed]

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