Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
The structure was elucidated in this paperNCBI PubMed ID: 33159946Publication DOI: 10.1016/j.ijbiomac.2020.11.005Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: johanna.kenyon
qut.edu.au
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Queensland University of Technology, Brisbane, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, PR China
KL55, KL74, and KL85 capsular polysaccharide (CPS) biosynthesis loci in Acinetobacter baumannii BAL_204, BAL_309, and LUH5543 genomes, respectively, are related and each contains genes for l-Rhap and d-GlcpA synthesis. The CPSs were isolated and studied by sugar analysis, Smith degradation, and 1H and 13C NMR spectroscopy. The K55 and K74 CPSs are built up of branched octasaccharide repeats (K units) containing one residue each of d-GlcpA and d-GlcpNAc and six residues of l-Rhap. The K55 unit differs from the K74 unit in the linkage between D-GlcpA and an l-Rhap residue in the K unit (1→3 versus 1→2) and linkage between K units. However, most K units in the isolated K74 CPS were modified by β-elimination of a side-chain α-l-Rhap-(1→3)-α-l-Rhap disaccharide from position 4 of GlcA to give 4-deoxy-l-threo-hex-4-enuronic acid (1:~3 ratio of intact and modified units). The K85 CPS has a branched heptasaccharide K unit similar to the K74 unit but with one fewer α-l-Rhap residue in the side chain. In contrast to previous findings on A. baumannii CPSs, each K locus includes fewer glycosyltransferase (Gtr) genes than the number required to form all linkages in the K units. Hence, one Gtr appears to be multifunctional catalysing formation of two 1→2 and one 1→3 linkages between the l-Rha residues.
Acinetobacter baumannii, capsular polysaccharide structure, β-elimination, capsule biosynthesis, rhamnosyltransferase, K locus
Structure type: polymer chemical repeating unit
Location inside paper: p. 1233, table 2, p. 1235, Fig.5, K74
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_133754,IEDB_135813,IEDB_135849,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_143254,IEDB_151531,IEDB_225177,IEDB_423153,IEDB_885823
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, anion-exchange chromatography, mild acid hydrolysis, Smith degradation, HPLC, GPC, bioinformatic analysis, HR-ESI-MS
Biosynthesis and genetic data: Grt79,Grt110, Grt145, Grt112, Grt112, Grt112, Grt82, Wzy(K74/K85)[ItrA3]
Comments, role: minor octasaccharide K unit (CPS from A. baumannii BAL_309)
Related record ID(s): 7856, 7857, 7858, 7860, 10828, 10879
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
3,2,3,2,2,4,3 aLRhap 103.5 71.5 71.5 73.5 70.4 18.0
3,2,3,2,2,4 aLRhap 101.0 71.3 79.6 72.6 69.8 18.0
3,2,3,2,2 bDGlcpA 105.5 76.0 80.3 76.7 77.1 175.4
3,2,3,2 aLRhap 102.2 81.7 71.2 73.5-73.6 70.3 17.9
3,2,3 aLRhap 102.0 79.7 71.2 73.5-73.6 70.3 18.1
3,2 aLRhap 103.6 71.3 78.9 72.9 70.4 18.0
3 aLRhap 101.1 81.2 71.2 73.5-73.6 70.3 17.9
2 Ac 176.2 23.6
bDGlcpN 102.2 57.0 83.1 70.0 77.1 62.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,3,2,2,4,3 aLRhap 5.03 4.05 3.83 3.46 3.79 1.29
3,2,3,2,2,4 aLRhap 4.72 4.01 3.78 3.50 4.47 1.28
3,2,3,2,2 bDGlcpA 4.59 3.51 3.86 3.67 3.79 -
3,2,3,2 aLRhap 5.24 4.13 3.88 3.46 3.72 1.26
3,2,3 aLRhap 5.19 4.04 3.92 3.47 3.78 1.30
3,2 aLRhap 4.85 4.09 3.80 3.55 3.77 1.28
3 aLRhap 5.04 3.76 3.84 3.45 3.98 1.24
2 Ac - 2.03
bDGlcpN 4.96 3.78 3.62 3.50 3.40 3.75-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,3,2,2,4,3 aLRhap 103.5/5.03 71.5/4.05 71.5/3.83 73.5/3.46 70.4/3.79 18.0/1.29
3,2,3,2,2,4 aLRhap 101.0/4.72 71.3/4.01 79.6/3.78 72.6/3.50 69.8/4.47 18.0/1.28
3,2,3,2,2 bDGlcpA 105.5/4.59 76.0/3.51 80.3/3.86 76.7/3.67 77.1/3.79
3,2,3,2 aLRhap 102.2/5.24 81.7/4.13 71.2/3.88 73.5-73.6/3.46 70.3/3.72 17.9/1.26
3,2,3 aLRhap 102.0/5.19 79.7/4.04 71.2/3.92 73.5-73.6/3.47 70.3/3.78 18.1/1.30
3,2 aLRhap 103.6/4.85 71.3/4.09 78.9/3.80 72.9/3.55 70.4/3.77 18.0/1.28
3 aLRhap 101.1/5.04 81.2/3.76 71.2/3.84 73.5-73.6/3.45 70.3/3.98 17.9/1.24
2 Ac 23.6/2.03
bDGlcpN 102.2/4.96 57.0/3.78 83.1/3.62 70.0/3.50 77.1/3.40 62.1/3.75-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,3,2,2,4,3 | aLRhap | 5.03 | 4.05 | 3.83 | 3.46 | 3.79 | 1.29 |
| 3,2,3,2,2,4 | aLRhap | 4.72 | 4.01 | 3.78 | 3.50 | 4.47 | 1.28 |
| 3,2,3,2,2 | bDGlcpA | 4.59 | 3.51 | 3.86 | 3.67 | 3.79 |
|
| 3,2,3,2 | aLRhap | 5.24 | 4.13 | 3.88 | 3.46 | 3.72 | 1.26 |
| 3,2,3 | aLRhap | 5.19 | 4.04 | 3.92 | 3.47 | 3.78 | 1.30 |
| 3,2 | aLRhap | 4.85 | 4.09 | 3.80 | 3.55 | 3.77 | 1.28 |
| 3 | aLRhap | 5.04 | 3.76 | 3.84 | 3.45 | 3.98 | 1.24 |
| 2 | Ac |
| 2.03 | |
| | bDGlcpN | 4.96 | 3.78 | 3.62 | 3.50 | 3.40 | 3.75
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,3,2,2,4,3 | aLRhap | 103.5 | 71.5 | 71.5 | 73.5 | 70.4 | 18.0 |
| 3,2,3,2,2,4 | aLRhap | 101.0 | 71.3 | 79.6 | 72.6 | 69.8 | 18.0 |
| 3,2,3,2,2 | bDGlcpA | 105.5 | 76.0 | 80.3 | 76.7 | 77.1 | 175.4 |
| 3,2,3,2 | aLRhap | 102.2 | 81.7 | 71.2 | 73.5
73.6 | 70.3 | 17.9 |
| 3,2,3 | aLRhap | 102.0 | 79.7 | 71.2 | 73.5
73.6 | 70.3 | 18.1 |
| 3,2 | aLRhap | 103.6 | 71.3 | 78.9 | 72.9 | 70.4 | 18.0 |
| 3 | aLRhap | 101.1 | 81.2 | 71.2 | 73.5
73.6 | 70.3 | 17.9 |
| 2 | Ac | 176.2 | 23.6 | |
| | bDGlcpN | 102.2 | 57.0 | 83.1 | 70.0 | 77.1 | 62.1 |
|
There is only one chemically distinct structure:
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Found 1 record.
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