Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella boydii [ICD11:
XN8RN ]
Publication DOI: 10.1016/j.tetasy.2011.08.004Journal NLM ID: 9010953Publisher: Oxford: Elsevier
Correspondence: A.K. Misra <akmisra69
rediffmail.com>
Institutions: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700054, India
An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14 is reported. A one-pot, two step iterative glycosylation and [3+2] block synthetic strategy have been adopted for the construction of the pentasaccharide derivative 11, which was then transformed into target compound 1 after a series of functional group transformations. The primary hydroxyl group has been selectively oxidized to a carboxylic acid functionality without affecting the secondary hydroxyl groups. HClO4-SiO2 has been used as a solid acid substitute in all glycosylation and functional group transformations. The yields were excellent in all glycosylation steps.
synthesis, O-antigen, Shigella boydii type 14
Structure type: polymer chemical repeating unit
Location inside paper: p.1390, fig. 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130646,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_140630,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_158533,IEDB_190606,IEDB_221845,IEDB_423153,SB_165,SB_166,SB_187,SB_195,SB_30,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, glycosylation
Synthetic data: chemical
Comments, role: published polymerization frame was shifted for conformity with other records.
Related record ID(s): 26905
NCBI Taxonomy refs (TaxIDs): 621Reference(s) to other database(s): GTC:G17781ZM, GlycomeDB:
3526
Show glycosyltransferases
There is only one chemically distinct structure:
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