Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 31422158Publication DOI: 10.1016/j.carres.2019.107766Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: A.V. Perepelov <andreivperepelov
gmail.com>
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institure of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China
O-polysaccharide (O-antigen) was isolated from the lipopolysaccharide of Vibrio cholerae O100 and studied by component analyses and 1D and 2D NMR spectroscopy. The following structure of the O-polysaccharide was established: →3)-β-d-QuipNAc4N(dHh)-(1→3)-α-d-Fucp4N(RHb)-(1→3)-α-l-FucpNAc-( 1→ where Hb and dHh indicate 3-hydroxybutanoyl and 3,5-dihydroxyhexanoyl, respectively. The O-antigen gene cluster of V. cholerae O100 has been sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in agreement with the OPS structure.
Lipopolysaccharide, O-antigen, O-polysaccharide, bacterial polysaccharide structure, 2, Vibrio cholerae, O-antigen gene cluster, 4-dihydroxypentanoic acid
Structure type: polymer chemical repeating unit
Location inside paper: abstract, table 1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141501,IEDB_141584,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_885822,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, GPC, alkaline deacylation, acid degradation, function analysis of gene clusters, sequencing, NMR analysis by GODDESS
Comments, role: V. cholerae O68 type strain (laboratory stock number G5588); deacylated OPS.
NCBI Taxonomy refs (TaxIDs): 666
Show glycosyltransferases
NMR conditions: in D2O at 338 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,3,4 Subst 178.5 77.4 37.9 76.7 21.0
3,4,3 bDGlcp 105.1 75.3 82.4 75.1 75.4 61.4
3,4,2 Ac 175.5-176.3 23.3-23.7
3,4 bDGalpN 103.1 52.8 81.2 69.3 75.8 62.2
3,2 Ac 175.5-176.3 23.3-23.7
3 aDGalpN 98.8 51.2 69.2 76.4 71.6 61.5
2 Ac 175.5-176.3 23.3-23.7
bDGlcpN 101.7 56.0 80.3 72.4 76.8 62.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,3,4 Subst - 5.23 1.79-2.90 4.65 1.44
3,4,3 bDGlcp 4.48 3.41 4.04 3.54 3.46 3.68-3.83
3,4,2 Ac - 2.02-2.04
3,4 bDGalpN 4.75 4.01 3.89 4.12 3.67 3.78-3.78
3,2 Ac - 2.02-2.04
3 aDGalpN 5.33 4.13 4.91 4.18 3.85 3.83-3.83
2 Ac - 2.02-2.04
bDGlcpN 4.94 3.75 3.68 3.59 3.38 3.71-3.88
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,3,4 Subst 77.4/5.23 37.9/1.79-2.90 76.7/4.65 21.0/1.44
3,4,3 bDGlcp 105.1/4.48 75.3/3.41 82.4/4.04 75.1/3.54 75.4/3.46 61.4/3.68-3.83
3,4,2 Ac 23.3-23.7/2.02-2.04
3,4 bDGalpN 103.1/4.75 52.8/4.01 81.2/3.89 69.3/4.12 75.8/3.67 62.2/3.78-3.78
3,2 Ac 23.3-23.7/2.02-2.04
3 aDGalpN 98.8/5.33 51.2/4.13 69.2/4.91 76.4/4.18 71.6/3.85 61.5/3.83-3.83
2 Ac 23.3-23.7/2.02-2.04
bDGlcpN 101.7/4.94 56.0/3.75 80.3/3.68 72.4/3.59 76.8/3.38 62.0/3.71-3.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,3,4 | Subst |
| 5.23 | 1.79
2.90 | 4.65 | 1.44 | |
| 3,4,3 | bDGlcp | 4.48 | 3.41 | 4.04 | 3.54 | 3.46 | 3.68
3.83 |
| 3,4,2 | Ac |
| 2.02
2.04 | |
| 3,4 | bDGalpN | 4.75 | 4.01 | 3.89 | 4.12 | 3.67 | 3.78
3.78 |
| 3,2 | Ac |
| 2.02
2.04 | |
| 3 | aDGalpN | 5.33 | 4.13 | 4.91 | 4.18 | 3.85 | 3.83
3.83 |
| 2 | Ac |
| 2.02
2.04 | |
| | bDGlcpN | 4.94 | 3.75 | 3.68 | 3.59 | 3.38 | 3.71
3.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,3,4 | Subst | 178.5 | 77.4 | 37.9 | 76.7 | 21.0 | |
| 3,4,3 | bDGlcp | 105.1 | 75.3 | 82.4 | 75.1 | 75.4 | 61.4 |
| 3,4,2 | Ac | 175.5
176.3 | 23.3
23.7 | |
| 3,4 | bDGalpN | 103.1 | 52.8 | 81.2 | 69.3 | 75.8 | 62.2 |
| 3,2 | Ac | 175.5
176.3 | 23.3
23.7 | |
| 3 | aDGalpN | 98.8 | 51.2 | 69.2 | 76.4 | 71.6 | 61.5 |
| 2 | Ac | 175.5
176.3 | 23.3
23.7 | |
| | bDGlcpN | 101.7 | 56.0 | 80.3 | 72.4 | 76.8 | 62.0 |
|
There is only one chemically distinct structure:
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