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Chemical Compound Review

Perosamine     (2S,3S,4R,5R)-4-amino-2,3,5- trihydroxy...

Synonyms: D-perosamine, AG-K-71391, CHEBI:32571, AC1L4PXH, CTK4G6895, ...
 
 
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Disease relevance of Perosamine

  • A putative pathway for perosamine biosynthesis is the first function encoded within the rfb region of Vibrio cholerae O1 [1].
  • Although, many studies show that this specific recognition results mainly from the ratios of alpha 1-2 and alpha 1-3 link between the different Brucella strain perosamine residues, little is known about the mAb recognising this O-antigen [2].
  • The structure of the O-polysaccharide from Pseudomonas stutzeri OX1 containing two different 4-acylamido-4,6-dideoxy-residues, tomosamine and perosamine [3].
  • The O-antigen of the gram negative bacteria Brucella is composed of an homopolymer of 4,6-dideoxy-4-formamido-alpha-D-mannopyranosyl (or perosamine) [2].
 

High impact information on Perosamine

  • Transposon mutagenesis of the putative perosamine biosynthesis genes in the rfb operon of V. cholerae 569B eliminates lipopolysaccharide (LPS) O-antigen biosynthesis but also leads to a specific defect in TCP export [4].
  • Mutants in the perosamine biosynthesis pathway of V. cholerae 569B result in an rfb phenotype with an LPS consisting only of core oligosaccharide and lipid A [5].
  • Vibrio cholerae O1 LPS terminal mono- and disaccharide elements were synthesized by reduction of the azido group in several 4-amino-4,6-dideoxy-D-mannose mono- and disaccharide derivatives, followed by coupling with 2, 4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline [6].
  • Method of study Immunization with synthetic derivatives of the carbohydrate moieties of V. cholerae lipopolysaccharide (LPS) coupled to different carrier proteins (neoglycoconjugates, NGC) has allowed dissection of the response to the disaccharide array of perosamine that represent either the Inaba or the Ogawa serotype [7].
  • Fetuses of goats in their last trimester of pregnancy were experimentally infected with Brucella abortus strain RB51, a stable rough mutant deficient in the perosamine O-chain content of its lipopolysaccharide [8].
 

Chemical compound and disease context of Perosamine

References

  1. A putative pathway for perosamine biosynthesis is the first function encoded within the rfb region of Vibrio cholerae O1. Stroeher, U.H., Karageorgos, L.E., Brown, M.H., Morona, R., Manning, P.A. Gene (1995) [Pubmed]
  2. Functional, molecular and structural characterisation of five anti-Brucella LPS mAb. Laurent, T.C., Mertens, P., Dierick, J.F., Letesson, J.J., Lambert, C., De Bolle, X. Mol. Immunol. (2004) [Pubmed]
  3. The structure of the O-polysaccharide from Pseudomonas stutzeri OX1 containing two different 4-acylamido-4,6-dideoxy-residues, tomosamine and perosamine. Leone, S., Izzo, V., Lanzetta, R., Molinaro, A., Parrilli, M., Di Donato, A. Carbohydr. Res. (2005) [Pubmed]
  4. Outer membrane translocation arrest of the TcpA pilin subunit in rfb mutants of Vibrio cholerae O1 strain 569B. Iredell, J.R., Manning, P.A. J. Bacteriol. (1997) [Pubmed]
  5. Translocation failure in a type-4 pilin operon: rfb and tcpT mutants in Vibrio cholerae. Iredell, J.R., Manning, P.A. Gene (1997) [Pubmed]
  6. Synthesis of terminal disaccharide elements corresponding to the Ogawa and Inaba antigenic determinant from Vibrio cholerae O1. Arencibia-Mohar, A., Ariosa-Alvarez, A., Madrazo-Alonso, O., González Abreu, E., García-Imia, L., Sierra-González, G., Verez-Bencomo, V. Carbohydr. Res. (1998) [Pubmed]
  7. B-cell responses to lipopolysaccharide epitopes: who sees what first - does it matter? Wade, W.F. Am. J. Reprod. Immunol. (2006) [Pubmed]
  8. Experimental infection of goat fetuses in utero with a stable, rough mutant of Brucella abortus. Roop, R.M., Jeffers, G., Bagchi, T., Walker, J., Enright, F.M., Schurig, G.G. Res. Vet. Sci. (1991) [Pubmed]
  9. The structure of the O-antigenic side chain of the lipopolysaccharide of Vibrio cholerae 569B (Inaba). Redmond, J.W. Biochim. Biophys. Acta (1979) [Pubmed]
 
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