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Duan Z, Senchenkova SN, Guo X, Perepelov AV, Shashkov AS, Liu B, Knirel YA
Structure and gene cluster of the O-antigen of Escherichia coli O156 containing a pyruvic acid acetal
Carbohydrate Research 430 (2016)
24-28
|
R-Pyr-(2-6:2-4)-a-D-Galp-(1-3)-+
|
-4)-a-L-Fucp-(1-6)-a-D-Galp-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Escherichia coli O156
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: enterohemorrhagic disease [ICD11:
1A03.3 
, ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 27177202Publication DOI: 10.1016/j.carres.2016.04.025Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel
gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
The lipopolysaccharide of Escherichia coli O156 was degraded under mild acidic and alkaline conditions and the resulting polysaccharides were studied by sugar analysis and (1)H and (13)C NMR spectroscopy. The following structure of the pentasaccharide repeating unit of the O-polysaccharide was established: where Rpyr indicates R-configurated pyruvic acid acetal. Minor O-acetyl groups also were present and tentatively localized on the Gal residues. The gene cluster for biosynthesis of the O-antigen of E. coli O156 was analyzed and shown to be consistent with the O-polysaccharide structure.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, pyruvic acid, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.27, chart 1, LPSOH
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151528,IEDB_151531,IEDB_151770,IEDB_152214,IEDB_174333,IEDB_190606,SB_7,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, mild alkaline degradation, NMR-1D, GPC, mild acid degradation, function analysis of gene clusters
Comments, role: O-deacylated lipopolysaccharide (LPSOH) derived by mild acid degradation of the LPS followed by O-deacylation; minor O-Ac tentatively localized on the Gal residues.
Related record ID(s): 11631
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,6,3,6 xRPyr 175.7 100.9 26.3
3,3,6,3 aDGalp 101.5 69.6 69.1 72.9 63.94 66.3
3,3,6 aLFucp 99.8 69.3 75.4 78.9 68.3 17.1
3,3 aDGalp 101.8 69.9 70.5 70.5 70.7 67.6
3 aLFucp 100.7 68.4 79.7 72.9 68.1 16.6
2 Ac 175.5 23.6
bDGlcpN 102.1 57.1 81.3 70.0 77.5 62.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,6,3,6 xRPyr - - 1.50
3,3,6,3 aDGalp 5.32 3.91 4.02 4.26 3.96 3.90-4.04
3,3,6 aLFucp 4.88 4.02 3.96 4.03 4.06 1.24
3,3 aDGalp 5.19 3.83 3.94 4.05 4.25 3.57-3.85
3 aLFucp 5.02 3.91 3.90 3.95 4.33 1.17
2 Ac - 2.01
bDGlcpN 4.63 3.84 3.69 3.52 3.39 3.67-3.87
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,6,3,6 xRPyr 26.3/1.50
3,3,6,3 aDGalp 101.5/5.32 69.6/3.91 69.1/4.02 72.9/4.26 63.94/3.96 66.3/3.90-4.04
3,3,6 aLFucp 99.8/4.88 69.3/4.02 75.4/3.96 78.9/4.03 68.3/4.06 17.1/1.24
3,3 aDGalp 101.8/5.19 69.9/3.83 70.5/3.94 70.5/4.05 70.7/4.25 67.6/3.57-3.85
3 aLFucp 100.7/5.02 68.4/3.91 79.7/3.90 72.9/3.95 68.1/4.33 16.6/1.17
2 Ac 23.6/2.01
bDGlcpN 102.1/4.63 57.1/3.84 81.3/3.69 70.0/3.52 77.5/3.39 62.3/3.67-3.87
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,6,3,6 | xRPyr |
|
| 1.50 | |
| 3,3,6,3 | aDGalp | 5.32 | 3.91 | 4.02 | 4.26 | 3.96 | 3.90
4.04 |
| 3,3,6 | aLFucp | 4.88 | 4.02 | 3.96 | 4.03 | 4.06 | 1.24 |
| 3,3 | aDGalp | 5.19 | 3.83 | 3.94 | 4.05 | 4.25 | 3.57
3.85 |
| 3 | aLFucp | 5.02 | 3.91 | 3.90 | 3.95 | 4.33 | 1.17 |
| 2 | Ac |
| 2.01 | |
| | bDGlcpN | 4.63 | 3.84 | 3.69 | 3.52 | 3.39 | 3.67
3.87 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,6,3,6 | xRPyr | 175.7 | 100.9 | 26.3 | |
| 3,3,6,3 | aDGalp | 101.5 | 69.6 | 69.1 | 72.9 | 63.94 | 66.3 |
| 3,3,6 | aLFucp | 99.8 | 69.3 | 75.4 | 78.9 | 68.3 | 17.1 |
| 3,3 | aDGalp | 101.8 | 69.9 | 70.5 | 70.5 | 70.7 | 67.6 |
| 3 | aLFucp | 100.7 | 68.4 | 79.7 | 72.9 | 68.1 | 16.6 |
| 2 | Ac | 175.5 | 23.6 | |
| | bDGlcpN | 102.1 | 57.1 | 81.3 | 70.0 | 77.5 | 62.3 |
|
There is only one chemically distinct structure:
Expand this record
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Duan Z, Senchenkova SN, Guo X, Perepelov AV, Shashkov AS, Liu B, Knirel YA
Structure and gene cluster of the O-antigen of Escherichia coli O156 containing a pyruvic acid acetal
Carbohydrate Research 430 (2016)
24-28
|
a-D-Galp-(1-3)-+
|
-4)-a-L-Fucp-(1-6)-a-D-Galp-(1-3)-a-L-Fucp-(1-3)-b-D-GlcpNAc-(1- |
Show graphically |
Escherichia coli O156
(Ancestor NCBI TaxID 562,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: enterohemorrhagic disease [ICD11:
1A03.3 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
The structure was elucidated in this paperNCBI PubMed ID: 27177202Publication DOI: 10.1016/j.carres.2016.04.025Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yknirel
gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Key Laboratory of Molecular Microbiology and Technology, Ministry of Education, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
The lipopolysaccharide of Escherichia coli O156 was degraded under mild acidic and alkaline conditions and the resulting polysaccharides were studied by sugar analysis and (1)H and (13)C NMR spectroscopy. The following structure of the pentasaccharide repeating unit of the O-polysaccharide was established: where Rpyr indicates R-configurated pyruvic acid acetal. Minor O-acetyl groups also were present and tentatively localized on the Gal residues. The gene cluster for biosynthesis of the O-antigen of E. coli O156 was analyzed and shown to be consistent with the O-polysaccharide structure.
O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, pyruvic acid, O-antigen gene cluster
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.27, chart 1, DPSOH
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142489,IEDB_144562,IEDB_145669,IEDB_150092,IEDB_151528,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_190606,SB_7,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, mild alkaline degradation, NMR-1D, GPC, mild acid degradation, function analysis of gene clusters
Comments, role: a modifed polysaccharide (DPSOH) derived by a longer mild acid degradation of the LPS followed by O-deacetylation.
Related record ID(s): 11264
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G60553JF
Show glycosyltransferases
NMR conditions: in D2O at 313 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3,6,3 aDGalp 101.0 69.9 70.7 70.8 72.7 62.7
3,3,6 aLFucp 101.8 69.3 74.7 79.4 68.5 17.2
3,3 aDGalp 99.9 70.0 70.5 70.5 70.7 67.3
3 aLFucp 101.0 68.4 79.4 72.9 68.1 16.6
2 Ac 175.7 23.5
bDGlcpN 102.4 57.1 81.2 69.8 77.4 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,3,6,3 aDGalp 5.31 3.81 3.96 4.02 4.21 3.73-3.78
3,3,6 aLFucp 5.21 4.05 4.04 4.14 4.10 1.27
3,3 aDGalp 4.90 3.83 3.96 4.06 4.27 3.57-3.87
3 aLFucp 5.04 3.91 3.91 3.98 4.36 1.17
2 Ac - 2.04
bDGlcpN 4.66 3.91 3.70 3.59 3.46 3.76-3.91
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,3,6,3 aDGalp 101.0/5.31 69.9/3.81 70.7/3.96 70.8/4.02 72.7/4.21 62.7/3.73-3.78
3,3,6 aLFucp 101.8/5.21 69.3/4.05 74.7/4.04 79.4/4.14 68.5/4.10 17.2/1.27
3,3 aDGalp 99.9/4.90 70.0/3.83 70.5/3.96 70.5/4.06 70.7/4.27 67.3/3.57-3.87
3 aLFucp 101.0/5.04 68.4/3.91 79.4/3.91 72.9/3.98 68.1/4.36 16.6/1.17
2 Ac 23.5/2.04
bDGlcpN 102.4/4.66 57.1/3.91 81.2/3.70 69.8/3.59 77.4/3.46 62.2/3.76-3.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,3,6,3 | aDGalp | 5.31 | 3.81 | 3.96 | 4.02 | 4.21 | 3.73
3.78 |
| 3,3,6 | aLFucp | 5.21 | 4.05 | 4.04 | 4.14 | 4.10 | 1.27 |
| 3,3 | aDGalp | 4.90 | 3.83 | 3.96 | 4.06 | 4.27 | 3.57
3.87 |
| 3 | aLFucp | 5.04 | 3.91 | 3.91 | 3.98 | 4.36 | 1.17 |
| 2 | Ac |
| 2.04 | |
| | bDGlcpN | 4.66 | 3.91 | 3.70 | 3.59 | 3.46 | 3.76
3.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3,6,3 | aDGalp | 101.0 | 69.9 | 70.7 | 70.8 | 72.7 | 62.7 |
| 3,3,6 | aLFucp | 101.8 | 69.3 | 74.7 | 79.4 | 68.5 | 17.2 |
| 3,3 | aDGalp | 99.9 | 70.0 | 70.5 | 70.5 | 70.7 | 67.3 |
| 3 | aLFucp | 101.0 | 68.4 | 79.4 | 72.9 | 68.1 | 16.6 |
| 2 | Ac | 175.7 | 23.5 | |
| | bDGlcpN | 102.4 | 57.1 | 81.2 | 69.8 | 77.4 | 62.2 |
|
There is only one chemically distinct structure:
Expand this record
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Calin O, Eller S, Hahm HS, Seeberger PH
Total Synthesis of the Escherichia coli O111 O-Specific Polysaccharide Repeating Unit
Chemistry: a European Journal 19(12) (2013)
3995-4002
|
a-Colp-(1-6)-+
|
a-Colp-(1-3)-a-D-Glcp-(1-4)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1--/5-aminopentyl/ |
Show graphically |
Escherichia coli O111
(NCBI TaxID 1055535,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 , ICD11:
SA55 ];
enterohemorrhagic disease [ICD11:
1A03.3 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 23447496Publication DOI: 10.1002/chem.201204394Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: peter.seeberger
mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476 Potsdam (Germany) and Institute for Chemistry and Biochemistry, Freie Universitat Berlin, Arnimallee 22, 14195 Berlin (Germany), Fax: (+49) 331-567-9302
The first total synthesis of the O-antigen pentasaccharide repeating unit from Gram-negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis-glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non-carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.
carbohydrates, Escherichia coli, antigens, vaccines, glycosylation
Structure type: oligomer
Location inside paper: p.3996, scheme.1, 1
Aglycon: 5-aminopentyl
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, chemical methods, MALDI-TOF MS
Synthetic data: chemical
Related record ID(s): 29928
NCBI Taxonomy refs (TaxIDs): 1055535Reference(s) to other database(s): GTC:G36088XJ
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Calin O, Eller S, Hahm HS, Seeberger PH
Total Synthesis of the Escherichia coli O111 O-Specific Polysaccharide Repeating Unit
Chemistry: a European Journal 19(12) (2013)
3995-4002
|
a-Colp-(1-3)-+
|
-4)-a-D-Glcp-(1-4)-a-D-Galp-(1-3)-b-D-GlcpNAc-(1-
|
a-Colp-(1-6)-+ |
Show graphically |
Escherichia coli O111
(NCBI TaxID 1055535,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 , ICD11:
SA55 ];
enterohemorrhagic disease [ICD11:
1A03.3 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 23447496Publication DOI: 10.1002/chem.201204394Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: peter.seeberger
mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476 Potsdam (Germany) and Institute for Chemistry and Biochemistry, Freie Universitat Berlin, Arnimallee 22, 14195 Berlin (Germany), Fax: (+49) 331-567-9302
The first total synthesis of the O-antigen pentasaccharide repeating unit from Gram-negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis-glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non-carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.
carbohydrates, Escherichia coli, antigens, vaccines, glycosylation
Structure type: polymer chemical repeating unit
Location inside paper: p.3995, fig.1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, chemical methods, MALDI-TOF MS
Synthetic data: chemical
Related record ID(s): 29436
NCBI Taxonomy refs (TaxIDs): 1055535Reference(s) to other database(s): GTC:G38677MM, GlycomeDB:
3515
Show glycosyltransferases
There is only one chemically distinct structure:
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