Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
The structure was elucidated in this paperNCBI PubMed ID: 35872312Publication DOI: 10.1016/j.ijbiomac.2022.07.136Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: M.V. Edelstein <Mikhail.Edelstein
antibiotic.ru>; J.J. Kenyon <johanna.kenyon
qut.edu.au>
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, M. M. Shemyakin and Y. A.Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 119997 Moscow, Russia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, 214019 Smolensk, Russia
The K98 capsular polysaccharide (CPS) from the Acinetobacter baumannii clinical isolate, REV-1184, was studied by sugar analysis and Smith degradation along with one- and two-dimensional 1H and 13C NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. The CPS was found to consist of linear tetrasaccharide repeats (K-units) that include one residue each of D-GlcpNAc, D-GalpNAc, 2-acetamido-2-deoxy-D-galacturonic acid (D-GalpNAcA), and 2-acetamido-2,6-dideoxy-D-glucose (N-acetylquinovosamine, D-QuipNAc), with the GalpNAc residue decorated with a (R)-configurated 4,6-pyruvic acid acetal group. The CPS has a similar composition to that of A. baumannii K4 but the topology of the tetrasaccharide K-unit is different (linear in K98 versus branched in K4). This was due to a difference in sequence for the Wzy polymerases encoded by the CPS biosynthesis gene clusters KL98 and KL4, with the WzyK98 polymerase forming a β-D-QuipNAc-(1→3)-D-GalpNAc linkage between the K98 units.
Acinetobacter baumannii, capsular polysaccharide, 2-acetamido-2, 6-dideoxy-d-glucose, 2-acetamido-2-deoxy-D-galacturonic acid, Pyruvic acid acetal, K locus
Structure type: polymer chemical repeating unit ; 70500
Location inside paper: p. 451, table 1, p. 452, Fig. 5B, Fig. 6
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation, HPLC, GPC, bioinformatic analysis, HR-ESI-MS, sequencing
Enzymes that release or process the structure: Ptr1,Gtr171, Gtr172, Gtr12, WzyK98[ItrB1]
Related record ID(s): 21017, 21018, 21019
NCBI Taxonomy refs (TaxIDs): 470
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,6,2 Ac 174.8-175.9 23.4-23.8
3,4,6,6 xRPyr 174.9 100.6 26.3
3,4,6 aDGalpN 98.9 49.4 75.5 78.8 73.1 66.4
3,4,2 Ac 174.8-175.9 23.4-23.8
3,4 aDGlcpN 99.7 55.0 72.3 71.1 72.2 66.6
3,2 Ac 174.8-175.9 23.4-23.8
3 aDGalpNA 98.5 50.8 68.0 79.8 72.0 173.7
2 Ac 174.8-175.9 23.4-23.8
bDQuipN 102.6 56.1 77.0 77.4 72.2 17.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,6,2 Ac - 1.94-2.04
3,4,6,6 xRPyr - - 1.54
3,4,6 aDGalpN 4.90 4.36 4.01 4.40 4.45 3.92-3.92
3,4,2 Ac - 1.94-2.04
3,4 aDGlcpN 5.36 3.90 3.78 3.56 4.21 3.58-3.99
3,2 Ac - 1.94-2.04
3 aDGalpNA 5.23 4.22 4.01 4.36 4.31 -
2 Ac - 1.94-2.04
bDQuipN 4.61 3.77 3.86 3.47 3.51 1.16
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,6,2 Ac 23.4-23.8/1.94-2.04
3,4,6,6 xRPyr 26.3/1.54
3,4,6 aDGalpN 98.9/4.90 49.4/4.36 75.5/4.01 78.8/4.40 73.1/4.45 66.4/3.92-3.92
3,4,2 Ac 23.4-23.8/1.94-2.04
3,4 aDGlcpN 99.7/5.36 55.0/3.90 72.3/3.78 71.1/3.56 72.2/4.21 66.6/3.58-3.99
3,2 Ac 23.4-23.8/1.94-2.04
3 aDGalpNA 98.5/5.23 50.8/4.22 68.0/4.01 79.8/4.36 72.0/4.31
2 Ac 23.4-23.8/1.94-2.04
bDQuipN 102.6/4.61 56.1/3.77 77.0/3.86 77.4/3.47 72.2/3.51 17.8/1.16
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,6,2 | Ac |
| 1.94
2.04 | |
| 3,4,6,6 | xRPyr |
|
| 1.54 | |
| 3,4,6 | aDGalpN | 4.90 | 4.36 | 4.01 | 4.40 | 4.45 | 3.92
3.92 |
| 3,4,2 | Ac |
| 1.94
2.04 | |
| 3,4 | aDGlcpN | 5.36 | 3.90 | 3.78 | 3.56 | 4.21 | 3.58
3.99 |
| 3,2 | Ac |
| 1.94
2.04 | |
| 3 | aDGalpNA | 5.23 | 4.22 | 4.01 | 4.36 | 4.31 |
|
| 2 | Ac |
| 1.94
2.04 | |
| | bDQuipN | 4.61 | 3.77 | 3.86 | 3.47 | 3.51 | 1.16 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,6,2 | Ac | 174.8
175.9 | 23.4
23.8 | |
| 3,4,6,6 | xRPyr | 174.9 | 100.6 | 26.3 | |
| 3,4,6 | aDGalpN | 98.9 | 49.4 | 75.5 | 78.8 | 73.1 | 66.4 |
| 3,4,2 | Ac | 174.8
175.9 | 23.4
23.8 | |
| 3,4 | aDGlcpN | 99.7 | 55.0 | 72.3 | 71.1 | 72.2 | 66.6 |
| 3,2 | Ac | 174.8
175.9 | 23.4
23.8 | |
| 3 | aDGalpNA | 98.5 | 50.8 | 68.0 | 79.8 | 72.0 | 173.7 |
| 2 | Ac | 174.8
175.9 | 23.4
23.8 | |
| | bDQuipN | 102.6 | 56.1 | 77.0 | 77.4 | 72.2 | 17.8 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
