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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11: XN8LS

]

The structure was elucidated in this paper
NCBI PubMed ID: 33159946
Publication DOI: 10.1016/j.ijbiomac.2020.11.005
Journal NLM ID: 7909578
Publisher: 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, K85
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: Grt78, Grt145, Grt112, Grt112, Grt112, Grt82, Wzy(K74/K85)[ItrA3]

Related record ID(s): 7856, 7857, 7858, 7859, 7860, 10828
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	aLRhap	101.0	71.5	71.4	73.4	69.8	17.9
3,2,3,2,2	bDGlcpA	105.4	75.9	80.5	76.6	77.3	175.3
3,2,3,2	aLRhap	102.1	81.5	71.2	73.6	70.2	17.8
3,2,3	aLRhap	102.0	79.6	71.2	73.5	70.3	18.0
3,2	aLRhap	103.4	71.3	78.8	72.9	70.4	17.9
3	aLRhap	101.0	81.0	71.2	73.6	70.3	17.8
2	Ac	175.5	23.8
	bDGlcpN	102.0	57.1	83.1	70.2	77.0	62.3


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,3,2,2,4	aLRhap	4.77	3.90	3.77	3.40	4.37	1.27
3,2,3,2,2	bDGlcpA	4.58	3.50	3.84	3.68	3.77	-
3,2,3,2	aLRhap	5.23	4.12	3.86	3.46	3.71	1.25
3,2,3	aLRhap	5.16	4.04	3.91	3.48	3.78	1.29
3,2	aLRhap	4.86	4.09	3.81	3.55	3.77	1.28
3	aLRhap	5.04	3.78	3.84	3.44	3.96	1.24
2	Ac	-	2.09
	bDGlcpN	4.96	3.78	3.64	3.49	3.40	3.79-3.92


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,2,3,2,2,4	aLRhap	101.0/4.77	71.5/3.90	71.4/3.77	73.4/3.40	69.8/4.37	17.9/1.27
3,2,3,2,2	bDGlcpA	105.4/4.58	75.9/3.50	80.5/3.84	76.6/3.68	77.3/3.77	
3,2,3,2	aLRhap	102.1/5.23	81.5/4.12	71.2/3.86	73.6/3.46	70.2/3.71	17.8/1.25
3,2,3	aLRhap	102.0/5.16	79.6/4.04	71.2/3.91	73.5/3.48	70.3/3.78	18.0/1.29
3,2	aLRhap	103.4/4.86	71.3/4.09	78.8/3.81	72.9/3.55	70.4/3.77	17.9/1.28
3	aLRhap	101.0/5.04	81.0/3.78	71.2/3.84	73.6/3.44	70.3/3.96	17.8/1.24
2	Ac		23.8/2.09
	bDGlcpN	102.0/4.96	57.1/3.78	83.1/3.64	70.2/3.49	77.0/3.40	62.3/3.79-3.92

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,2,3,2,2,4	aLRhap	4.77	3.90	3.77	3.40	4.37	1.27
3,2,3,2,2	bDGlcpA	4.58	3.50	3.84	3.68	3.77
3,2,3,2	aLRhap	5.23	4.12	3.86	3.46	3.71	1.25
3,2,3	aLRhap	5.16	4.04	3.91	3.48	3.78	1.29
3,2	aLRhap	4.86	4.09	3.81	3.55	3.77	1.28
3	aLRhap	5.04	3.78	3.84	3.44	3.96	1.24
2	Ac		2.09
	bDGlcpN	4.96	3.78	3.64	3.49	3.40	3.79 3.92

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,3,2,2,4	aLRhap	101.0	71.5	71.4	73.4	69.8	17.9
3,2,3,2,2	bDGlcpA	105.4	75.9	80.5	76.6	77.3	175.3
3,2,3,2	aLRhap	102.1	81.5	71.2	73.6	70.2	17.8
3,2,3	aLRhap	102.0	79.6	71.2	73.5	70.3	18.0
3,2	aLRhap	103.4	71.3	78.8	72.9	70.4	17.9
3	aLRhap	101.0	81.0	71.2	73.6	70.3	17.8
2	Ac	175.5	23.8
	bDGlcpN	102.0	57.1	83.1	70.2	77.0	62.3

There is only one chemically distinct structure:

*O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@H](O[C@H]3[C@H](O[C@@H]4[C@@H](O)[C@H](C)O[C@@H](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](CO)O[C@@H](*)[C@@H]6NC(C)=O)O[C@@H](C)[C@H](O)[C@H]5O)[C@@H]4O)O[C@@H](C)[C@H](O)[C@H]3O)O[C@@H](C)[C@H](O)[C@H]2O)O[C@H](C(=O)O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize