Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Shigella dysenteriae [ICD11:
XN285 
]
Publication DOI: 10.1016/0008-6215(93)80073-NJournal NLM ID: 0043535Publisher: Elsevier
Institutions: NIDDK, National Institutes of Health, Bethesda, MD, USA
Methyl O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-l-rhamnopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-α-l-rhamnopyranoside was treated with dichloromethyl methyl ether and ZnCl2 to give O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-l-rhamnopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-α-l-rhamnopyranosyl chloride. Similar treatment of methyl O-(3,4-,6-tri-O-acetyl-2-azido-2-deoxy-α-d-glycopyranosyl)-(1 → →3)-2,4-di-O-benzoyl-α-l-rhamnopyranoside (13) gave crystalline O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-glucopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-α-l-rhamnopyranosyl chloride (14), which was also obtained by treatment of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxoy-α-d-glucopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-1-thio-α,l-rhamnopyranoside (12) with chlorine. In contrast to the conversion 12 → 14, which was stereospecific, the reaction of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-glucopyranosyl)-(1 → 3)-(O-2,4-di-O-benzoyl-α-l-rhamnopyranosyl)-(1 → 3)-2,4-di-O-benzoyl-1-thio-α-l-rhamnopyranoside with chlorine gave a mixture of the corresponding α-(16) and β-(17) glycosyl chlorides. Condensation of the mixed chlorides 16 and 17 with 1,3,4,6-tetra-O-acetyl-α-d-galactopyranose, followed by reduction-acetylation of the product, gave a fully protected derivative of the tetrasaccharide α-d-Glcp NAc-(1 → 3)-α-l-Rhap-(1 → 3)-α-l-Rhap-(1 → 2)-α-d-Galp.
Structure type: polymer chemical repeating unit
Location inside paper: p.219
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137483,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: chemical synthesis
NCBI Taxonomy refs (TaxIDs): 984897Reference(s) to other database(s): GTC:G76746EO, GlycomeDB:
6223
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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