Taxonomic group: bacteria / Chlamydiae
(Phylum: Chlamydiae)
Associated disease: infection due to Chlamydia [ICD11:
XN27H 
]
The structure was elucidated in this paperNCBI PubMed ID: 1382853Publication DOI: 10.1016/s0008-6215(00)90571-8Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Carlsberg Laboratory, Valby, Denmark
The 1H- and 13C-NMR parameters, chemical shifts and coupling constants, for the pentasaccharide of the genus-specific epitope of Chlamydia lipopolysaccharide and related di-, tri-, and tetra-saccharides have been measured and assigned completely using 1D and 2D techniques, and their structures have been confirmed. NOE experiments indicated the preferred conformation of the pentasaccharide and the component oligosaccharides. The 3JH,H demonstrate a change in conformation by rotation of the C-6-C-7 bond of the side chain of the (2→8)-linked Kdo (unit b) in α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-GlcN-(1→6)-GlcNol, α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→6)-β-GlcNAc-(1→O)-allyl, and α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo-(2→O)-allyl relative to that preferred in α-Kdo-(2→4)-α-Kdo-(2→6)-β-GlcNAc-(1→O)-allyl, α-Kdo-(2→8)-α-Kdo-(2→O)-allyl, α-Kdo-(2→4)-α-Kdo-(2→O)-allyl, and α-Kdo-(2→6)-β-GlcNAc-(1→O)-allyl, irrespective of the size of the aglycon, e.g., allyl or β-D-GlcN residues. The conformational results have been substantiated by computer calculations using the HSEA approach.
Structure type: oligomer
Location inside paper: p. 215, structure 1
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130657,IEDB_130658,IEDB_130659,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, NMR-2D
Related record ID(s): 116692, 116693, 116694, 116695, 116696, 116697, 131774
NCBI Taxonomy refs (TaxIDs): 810Reference(s) to other database(s): GTC:G18922QS, GlycomeDB:
6226
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
6,6,4,8 aXKdop 175.6 100.5 35.0 66.8 67.2 72.2 70.2 63.9
6,6,4 aXKdop 176.0 100.7 35.3 66.7 68.0 72.4 71.5 64.0
6,6 aXKdop 176.4 101.6 34.3 70.9 65.9 72.2 70.4 64.1
6 bDGlcpN 104.5 57.5 76.8 71.4 75.2 62.9
xDGlcN-ol 63.7 54.7 70.6 71.8 70.6 72.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
6,6,4,8 aXKdop - - 1.778-2.028 4.080 4.062 3.670 3.920 3.710-3.919
6,6,4 aXKdop - - 1.798-2.120 4.069 4.077 3.789 4.170 3.581-3.581
6,6 aXKdop - - 1.885-2.019 4.056 4.103 3.666 3.903 3.611-3.884
6 bDGlcpN 4.419 2.631 3.364 3.329 3.592 3.475-3.600
xDGlcN-ol 3.549-3.685 3.022 3.799 3.717 3.896 3.726-4.112
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
6,6,4,8 aXKdop 35.0/1.778-2.028 66.8/4.080 67.2/4.062 72.2/3.670 70.2/3.920 63.9/3.710-3.919
6,6,4 aXKdop 35.3/1.798-2.120 66.7/4.069 68.0/4.077 72.4/3.789 71.5/4.170 64.0/3.581-3.581
6,6 aXKdop 34.3/1.885-2.019 70.9/4.056 65.9/4.103 72.2/3.666 70.4/3.903 64.1/3.611-3.884
6 bDGlcpN 104.5/4.419 57.5/2.631 76.8/3.364 71.4/3.329 75.2/3.592 62.9/3.475-3.600
xDGlcN-ol 63.7/3.549-3.685 54.7/3.022 70.6/3.799 71.8/3.717 70.6/3.896 72.8/3.726-4.112
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 6,6,4,8 | aXKdop |
|
| 1.778
2.028 | 4.080 | 4.062 | 3.670 | 3.920 | 3.710
3.919 |
| 6,6,4 | aXKdop |
|
| 1.798
2.120 | 4.069 | 4.077 | 3.789 | 4.170 | 3.581
3.581 |
| 6,6 | aXKdop |
|
| 1.885
2.019 | 4.056 | 4.103 | 3.666 | 3.903 | 3.611
3.884 |
| 6 | bDGlcpN | 4.419 | 2.631 | 3.364 | 3.329 | 3.592 | 3.475
3.600 | |
| | xDGlcN-ol | 3.549
3.685 | 3.022 | 3.799 | 3.717 | 3.896 | 3.726
4.112 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 6,6,4,8 | aXKdop | 175.6 | 100.5 | 35.0 | 66.8 | 67.2 | 72.2 | 70.2 | 63.9 |
| 6,6,4 | aXKdop | 176.0 | 100.7 | 35.3 | 66.7 | 68.0 | 72.4 | 71.5 | 64.0 |
| 6,6 | aXKdop | 176.4 | 101.6 | 34.3 | 70.9 | 65.9 | 72.2 | 70.4 | 64.1 |
| 6 | bDGlcpN | 104.5 | 57.5 | 76.8 | 71.4 | 75.2 | 62.9 | |
| | xDGlcN-ol | 63.7 | 54.7 | 70.6 | 71.8 | 70.6 | 72.8 | |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
