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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)

NCBI PubMed ID: 858877
Publication DOI: 10.1021/ja00453a049
Journal NLM ID: 7503056
Publisher: American Chemical Society
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Stockholm, Sweden

The structure of the extracellular polysaccharide from Rhizobium meliloti, a microsymbiont in the nitrogen fixing symbiosis, has been investigated. The polysaccharide contains a terminal β-D-glucopyranosyl group with pyruvic acid ketalically linked to its 4 and 6 positions. After removal of this substituent from the methylated polysaccharide the four sugar residues in the side chain were removed sequentially by specific degradations; each of these steps involved oxidation, β-elimination by treatment with base, and, when necessary, acid hydrolysis under mild conditions. The result of each degradation was fol- lowed by trideuteriomethylation, hydrolysis, and analysis of the product by GLC/MS. The sequence of the sugar residues in the main chain was determined using a modified Smith degradation in which the polyalcohol, obtained after periodate oxidation-borohydride reduction, was methylated before the mild acid hydrolysis. As a result of these studies, it is concluded that the polysaccharide is composed of octasaccharide repeating units with the structure 25.

Structure type: polymer chemical repeating unit
Location inside paper: compound 25, p. 3814
Trivial name: succinoglycan
Compound class: EPS
Contained glycoepitopes: IEDB_135614,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_158555,IEDB_190606,IEDB_241101,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: methylation, acid hydrolysis, GLC, Smith degradation, periodate oxidation, GLC/MS

Related record ID(s): 3753, 116122, 116456, 139862, 147635
NCBI Taxonomy refs (TaxIDs): 382
Show glycosyltransferases

There is only one chemically distinct structure:

[*]O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](CO[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8O[C@@H]9COC(C)(C(=O)O)O[C@H]9[C@H](O)[C@H]8O)[C@H]7O)[C@H]6O)[C@@H](O)[C@H](O)[C@H]5O)O[C@@H]([*])[C@H](O)[C@H]4O)[C@@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize