Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Bos taurus; Sus scrofa
Associated disease: hemorrhagic colitis (HC) [ICD11:
1A40.0 
];
hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 28489404Publication DOI: 10.1021/acs.joc.7b00561Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: ghoshrina
yahoo.com; ghosh_rina
hotmail.com
Institutions: Department of Chemistry, Jadavpur University, Kolkata 700 032, India
Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysaccharide of Escherichia coli 120, as its p-methoxyphenyl glycoside, have been achieved utilizing one-pot sequential glycosylation technique. The glycosylations have been accomplished either by the activation of the thioglycosides using NIS in the presence of FeCl3 or by a preactivation by Ph2SO, TTBP, Tf2O and the activation of the trichloroacetimidates using FeCl3 alone or TMSOTf. Most of the intermediate steps are high yielding, and the stereo outcomes of the glycosylation steps were excellent. The syntheses of the targeted pentasaccharide have been performed with both three- and four-component one-pot sequential glycosylation reactions, and in both cases the orthogonal glycosylations are carried out utilizing catalytic activity of FeCl3. A late stage TEMPO-mediated regioselective oxidation has been performed to achieve the required uronic acid motif.
O-antigen, pentasaccharide, glycosylation, Escherichia coli 120
Structure type: polymer chemical repeating unit
Location inside paper: p.5752, fig.1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_130669,IEDB_133754,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_140630,IEDB_141794,IEDB_144990,IEDB_151528,IEDB_167071,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, UV, glycosylation, 1H ESI-TOF-MS
Related record ID(s): 12186
NCBI Taxonomy refs (TaxIDs): 2072455Reference(s) to other database(s): GTC:G34052RL
Show glycosyltransferases
There is only one chemically distinct structure:
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Bos taurus; Sus scrofa
Associated disease: hemorrhagic colitis (HC) [ICD11:
1A40.0 ];
hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 28489404Publication DOI: 10.1021/acs.joc.7b00561Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: ghoshrina
yahoo.com; ghosh_rina
hotmail.com
Institutions: Department of Chemistry, Jadavpur University, Kolkata 700 032, India
Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysaccharide of Escherichia coli 120, as its p-methoxyphenyl glycoside, have been achieved utilizing one-pot sequential glycosylation technique. The glycosylations have been accomplished either by the activation of the thioglycosides using NIS in the presence of FeCl3 or by a preactivation by Ph2SO, TTBP, Tf2O and the activation of the trichloroacetimidates using FeCl3 alone or TMSOTf. Most of the intermediate steps are high yielding, and the stereo outcomes of the glycosylation steps were excellent. The syntheses of the targeted pentasaccharide have been performed with both three- and four-component one-pot sequential glycosylation reactions, and in both cases the orthogonal glycosylations are carried out utilizing catalytic activity of FeCl3. A late stage TEMPO-mediated regioselective oxidation has been performed to achieve the required uronic acid motif.
O-antigen, pentasaccharide, glycosylation, Escherichia coli 120
Structure type: oligomer ; 923.3005 [M+Na]+
C
37H
56O
25Location inside paper: p.5752, fig.2, p.5756, scheme 8, compound 1
Aglycon: p-methoxyphenyl
Compound class: O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130669,IEDB_133754,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, UV, glycosylation, 1H ESI-TOF-MS
Synthetic data: chemical
Related record ID(s): 11942
NCBI Taxonomy refs (TaxIDs): 2072455Reference(s) to other database(s): GTC:G12824WQ
Show glycosyltransferases
NMR conditions: in D2O
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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