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Perepelov AV, Naumenko OI, Senchenkova SN, Shashkov AS, Chizhov AO, Knirel YA
Structure of the O-polysaccharide of Escherichia coli O60
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 67(11) (2018)
2131-2134
|
a-D-Galp-(1-3)-+
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-4)-b-D-Galp-(1- |
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Escherichia coli O60
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea (escherichiosis) [ICD11:
ME05.1 
, ICD11:
SA55 , ICD11:
XN6P4 ];
enterocolitis [ICD11:
1A40.Z ];
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 paperPublication DOI: 10.1007/s11172-018-2340-zJournal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: yknirel
gmail.com
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Structure of the O-polysaccharide (O-antigen) of Escherichia coli O60 was studied by sugar analysis, partial solvolysis with CF3CO2H, and 1D and 2D 1H and 13C NMR spectroscopy. The O-polysaccharide was found to consist of D-galactose and L-rhamnose. The structure of its branched tetrasaccharide repeating unit was established, which is unique among known bacterial polysaccharide structures.
Lipopolysaccharide, O-antigen, Escherichia, Escherichia coli, bacterial polysaccharide structure, solvolysis
Structure type: polymer chemical repeating unit
Location inside paper: p.2134, fig.3
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_133754,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, ESI-MS, acid hydrolysis, mild acid hydrolysis, GC, GPC, solvolysis with trifluoroacetic acid
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G82615LC
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NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,2 aLRhap 100.1 79.5 70.7 73.7 70.9 17.9
4,3 aDGalp 102.2 69.7 70.8 70.7 73.3 62.8
4 aLRhap 101.6 76.3 78.8 73.3 70.9 17.6
bDGalp 104.3 71.6 72.9 78.9 76.7 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,2 aLRhap 5.28 4.21 3.84 3.48 3.86 1.34
4,3 aDGalp 5.31 3.86 3.83 3.99 3.96 3.73-3.80
4 aLRhap 4.84 4.27 4.02 3.71 4.17 1.27
bDGalp 4.48 3.58 3.78 4.01 3.76 3.76-3.76
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,2 aLRhap 100.1/5.28 79.5/4.21 70.7/3.84 73.7/3.48 70.9/3.86 17.9/1.34
4,3 aDGalp 102.2/5.31 69.7/3.86 70.8/3.83 70.7/3.99 73.3/3.96 62.8/3.73-3.80
4 aLRhap 101.6/4.84 76.3/4.27 78.8/4.02 73.3/3.71 70.9/4.17 17.6/1.27
bDGalp 104.3/4.48 71.6/3.58 72.9/3.78 78.9/4.01 76.7/3.76 62.0/3.76-3.76
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,2 | aLRhap | 5.28 | 4.21 | 3.84 | 3.48 | 3.86 | 1.34 |
| 4,3 | aDGalp | 5.31 | 3.86 | 3.83 | 3.99 | 3.96 | 3.73
3.80 |
| 4 | aLRhap | 4.84 | 4.27 | 4.02 | 3.71 | 4.17 | 1.27 |
| | bDGalp | 4.48 | 3.58 | 3.78 | 4.01 | 3.76 | 3.76
3.76 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,2 | aLRhap | 100.1 | 79.5 | 70.7 | 73.7 | 70.9 | 17.9 |
| 4,3 | aDGalp | 102.2 | 69.7 | 70.8 | 70.7 | 73.3 | 62.8 |
| 4 | aLRhap | 101.6 | 76.3 | 78.8 | 73.3 | 70.9 | 17.6 |
| | bDGalp | 104.3 | 71.6 | 72.9 | 78.9 | 76.7 | 62.0 |
|
There is only one chemically distinct structure:
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Santra A, Si A, Kar RK, Bhunia A, Misra AK
Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13
Carbohydrate Research 391 (2014)
9-15
|
a-D-Glcp-(1-2)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1--/p-methoxyphenyl/ |
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Escherichia coli O13
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea (escherichiosis) [ICD11:
ME05.1 , ICD11:
SA55 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 24736048Publication DOI: 10.1016/j.carres.2014.03.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: akmisra69
gmail.com (A.K. Misra)
Institutions: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700 054, India
Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O13 strain has been achieved using a straightforward linear synthetic strategy. Similar reaction conditions have been used for all glycosylations as well as protective group manipulations. All intermediate steps are high yielding and the glycosylation steps are stereoselective. The synthesized pentasaccharide was subjected to conformational analysis using 2D ROESY NMR spectral analysis and molecular dynamics (MD) simulation to get detailed information on conformation of the molecule in aqueous solution.
O-antigen, Escherichia coli, conformational analysis, pentasaccharide, molecular dynamics simulation
Structure type: oligomer ; 950.3 [M+Na]+
C
39H
61NO
24Location inside paper: p.10, fig.2, compound 1
Aglycon: p-methoxyphenyl
Trivial name: repeating unit O-antigen
Contained glycoepitopes: IEDB_133753,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, conformation analysis, chemical synthesis, chemical methods, MD simulations, glycosylation, molecular modeling
Synthetic data: chemical
3D data: 3D data
Related record ID(s): 30445
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G47479JT
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1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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Santra A, Si A, Kar RK, Bhunia A, Misra AK
Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13
Carbohydrate Research 391 (2014)
9-15
|
a-D-Glcp-(1-2)-+
|
-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Escherichia coli O13
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea (escherichiosis) [ICD11:
ME05.1 , ICD11:
SA55 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 24736048Publication DOI: 10.1016/j.carres.2014.03.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: akmisra69
gmail.com (A.K. Misra)
Institutions: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata 700 054, India
Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O13 strain has been achieved using a straightforward linear synthetic strategy. Similar reaction conditions have been used for all glycosylations as well as protective group manipulations. All intermediate steps are high yielding and the glycosylation steps are stereoselective. The synthesized pentasaccharide was subjected to conformational analysis using 2D ROESY NMR spectral analysis and molecular dynamics (MD) simulation to get detailed information on conformation of the molecule in aqueous solution.
O-antigen, Escherichia coli, conformational analysis, pentasaccharide, molecular dynamics simulation
Structure type: suggested polymer biological repeating unit
Location inside paper: p.10, fig.1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, conformation analysis, chemical synthesis, chemical methods, MD simulations, glycosylation, molecular modeling
Synthetic data: chemical
Comments, role: chemical repeat frame is different in the paper
3D data: 3D data
Related record ID(s): 329, 11565, 25391, 28868, 30126
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G58114KG
Show glycosyltransferases
There is only one chemically distinct structure:
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