Abstract
The earlier established structures of the acidic O-specific polysaccharides from two typical strains of the Shigella dysenteriae bacterium were revised using modern NMR spectroscopy techniques. In particular, the configurations of the glycosidic linkages of GlcNAc (S. dysenteriae type 4) and mannose (S. dysenteriae type 5) residues were corrected. In addition, the location of the sites of non-stoichiometric O-acetylation in S. dysenteriae type 4 was determined: the lateral fucose residue was shown to be occasionally O-acetylated; also, theposition of the O-acetyl group present at the stoichiometric quantity in S. dysenteriae type 5 was corrected. The revised structures of the polysaccharides studied are shown below. The known identity of the O-specific polysaccharide structures of S. dysenteriae type 5 and Escherichia coli O58 was confirmed by 13C NMR spectroscopy and, hence, the structure of the E. coli O58 polysaccharide should be revised in the same manner.
where L-Rhap3Rlac2Ac is 2-O-acetyl-3-O-[(R-1-carboxyethyl]-L-rhamnose
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Abbreviations
- LPS:
-
lipopolysaccharide
- OSP:
-
O-specific polysaccharide
- DPS:
-
O-deacetylated polysaccharide
- COSY:
-
correlation spectroscopy
- EryA:
-
erythronic acid
- HMBC:
-
a heteronuclear correlation through several bonds
- HSQC:
-
a heteronuclear spectroscopy with one-quantum coherence transfer
- ROESY:
-
spectroscopy of nuclear Overhauser effect in a rotating coordinate system
- TOCSY:
-
total correlation spectroscopy
References
Perepelov, A.V., Senchenkova, S.N., Shashkov, A.S., Liu, V., Feng, L., Wang, L., and Knirel, Y.A., Bioorg. Khim., 2008, vol. 34, pp. 121–128; Rus. J. Bioorg. Chem., 2008, vol. 34, pp. 110–117.
Jonsson, K.H., Weintraub, A., and Widmalm, G., Carbohydr. Res., 2006, vol. 341, pp. 2986–2989.
Senchenkova, S.N., Feng, L., Yang, J., Shashkov, A.S., Cheng, J., Liu, D., Knirel, Y.A., Reeves, P., Jin, Q., Ye, Q., and Wang, L., J. Bacteriol., 2005, vol. 187, pp. 2551–2554.
Duus, J.O., Gotfredsen, C.H., and Bock, K., Chem. Rev., 2000, vol. 100, pp. 4589–4614.
Dmitriev, B.A., L’vov, V.L., Kochetkov, N.K., and Gofman, I.L., Bioorg. Khim., 1977, vol. 23, pp. 1226–1233.
Jansson, P.-E., Kenne, L., and Widmalm, G., Carbohydr. Res., 1989, vol. 188, pp. 169–191.
Knirel, Y.A., Shashkov, A.S., Senchenkova, S.N., Merino, S., and Tomas, J.M., Carbohydr. Res., 2002, vol. 337, pp. 1381–1386.
Perepelov, A.V., Liu, B., Senchenkova, S.N., Shashkov, A.S., Feng, L., Knirel, Yu.A., and Wang, L., Carbohydr. Res., 2007 (in press).
Linnerborg, M., Weintraub, A., and Widmalm, G., Eur. J. Biochem., 1999, vol. 266, pp. 246–251.
Kochetkov, N.K., Dmitriev, B.A., and Backinowsky, L.V., Carbohydr. Res., 1976, vol. 51, pp. 229–237.
Dmitriev, B.A., Backinowsky, L.V., Knirel, Y.A., Kochetkov, N.K., and Hofman, I.L., Eur. J. Biochem., 1977, vol. 78, pp. 381–387.
Jansson, P.-E., Kenne, L., and Schweda, E., J. Chem. Soc., Perkins Trans. 1, 1987, pp. 377–383.
Dmitriev, B.A., Knirel, Y.A., Kochetkov, N.K., Jann, B., and Jann, K., Eur. J. Biochem., 1977, vol. 79, pp. 111–115.
Robbins, P.W. and Uchida, T., Biochemistry, 1962, vol. 1, pp. 323–335.
Westphal, O. and Jann, K., Methods Carbohydr. Chem., 1965, vol. 5, pp. 83–91.
Conrad, H.E., Methods Carbohydr. Chem., 1972, vol. 6, pp. 361–364.
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Original Russian Text © A.V. Perepelov, S.N. Senchenkova, A.S. Shashkov, Yu. A. Knirel, B. Liu, L. Feng, L. Wang, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 4, pp. 513–521.
For communication 40, see [1].
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Perepelov, A.V., Senchenkova, S.N., Shashkov, A.S. et al. Antigenic polysaccharides of bacteria: 41. Structures of the O-specific polysaccharides of Shigella dysenteriae types 4 and 5 revised by NMR spectroscopy. Russ J Bioorg Chem 34, 460–467 (2008). https://doi.org/10.1134/S1068162008040109
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DOI: https://doi.org/10.1134/S1068162008040109