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

]

The structure was elucidated in this paper
Publication DOI: 10.1016/j.carres.2019.04.008
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: J.J. Kenyon <johanna.kenyon

qut.edu.au>
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russiag Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia

Acinetobacter baumannii isolate LUH5553 carries the KL90 capsule gene cluster, which includes genes for three glycosyltransferases (Gtrs) and the ItrA3 initiating transferase, as well as a set of genes for synthesis of a higher sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic (di-N-acetylpseudaminic) acid (Pse5Ac7Ac). The K90 capsular polysaccharide (CPS) has a tetrasaccharide repeat (K90 unit), which begins with d-GlcpNAc and contains Pse5Ac7Ac. The higher sugar was cleaved by mild acid hydrolysis of the CPS, and structures of the initial and modified polysaccharides were established by 1D and 2D 1H and 13C NMR spectroscopy. K90 contains α-d-Galp-(1-6)-d-GlcpNAc and α-d-GlcpNAc-(1-3)-d-GlcpNAc fragments, and formation of these glycosidic linkages is catalysed respectively by Gtr14 and Gtr15. The gtr14 and gtr15 genes occur in several A. baumannii KL gene clusters, including KL5 and KL7 that carry itrA2 rather than itrA3. As ItrA2 introduces d-GalpNAc rather than d-GlcpNAc as the first monosaccharide, Gtr15 can transfer d-GlcpNAc to either of these amino sugars, suggesting that this enzyme has relaxed specificity. Consequently, the third, novel glycosyltransferase, Gtr163, forms the β-(2-3) linkage between Pse5Ac7Ac and d-Galp. Wzy polymerases encoded by KL90 and KL7 are 54% identical and form the same linkage between the K units to give branched polysaccharides with the same main chain but different disaccharide side chains, β-Pse5Ac7Ac-(2-3)-d-Galp in K90 and α-Leg5Ac7Ac-(2-6)-d-Galp in K7.

Acinetobacter baumannii, capsular polysaccharide, Di-N-Acetylpseudaminic acid, KL90 gene cluster

Structure type: polymer chemical repeating unit
Location inside paper: table 1, fig.3B, K90
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_838988,SB_7

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, GPC, bioinformatic analysis, mild acid hydroysis
Enzymes that release or process the structure: Gtr163, Gtr14, Gtr15 glycosyltransferases, Wzy(K90)[ItrA3]
Biosynthesis and genetic data: WafA, WafB, WafC, WeeH
Comments, role: A. baumannii LUH5553 (laboratory stock number G4785).

Related record ID(s): 1102, 2272, 2274
NCBI Taxonomy refs (TaxIDs): 470
Reference(s) to other database(s): GTC:G72625RM
Show glycosyltransferases

NMR conditions: in D2O at 333 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,2	Ac	174.5-175.9	23.0-24.0
3,6,3,5	Ac	174.5-175.9	23.0-24.0
3,6,3,7	Ac	174.5-175.9	23.0-24.0
3,6,3	bXPsep	?	?	37.0	67.9	49.6	74.6	55.0	70.2	18.7
3,6	aDGalp	99.7	68.5	74.0	69.1	72.0	62.3
3	aDGlcpN	98.4	53.7	80.9	72.2	72.3	66.8
2	Ac	174.5-175.9	23.0-24.0
	bDGlcpN	101.7	55.8	79.9	69.6	76.8	61.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,2	Ac	-	1.92-2.05
3,6,3,5	Ac	-	1.92-2.05
3,6,3,7	Ac	-	1.92-2.05
3,6,3	bXPsep	-	-	1.66-2.53	3.86	4.19	3.87	3.98	4.11	1.21
3,6	aDGalp	4.99	3.85	4.34	4.01	3.89	3.61-3.65
3	aDGlcpN	5.36	4.08	3.76	3.68	3.75	3.69-4.03
2	Ac	-	1.92-2.05
	bDGlcpN	4.61	3.77	3.78	3.69	3.48	3.75-3.90


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
3,2	Ac		23.0-24.0/1.92-2.05
3,6,3,5	Ac		23.0-24.0/1.92-2.05
3,6,3,7	Ac		23.0-24.0/1.92-2.05
3,6,3	bXPsep			37.0/1.66-2.53	67.9/3.86	49.6/4.19	74.6/3.87	55.0/3.98	70.2/4.11	18.7/1.21
3,6	aDGalp	99.7/4.99	68.5/3.85	74.0/4.34	69.1/4.01	72.0/3.89	62.3/3.61-3.65
3	aDGlcpN	98.4/5.36	53.7/4.08	80.9/3.76	72.2/3.68	72.3/3.75	66.8/3.69-4.03
2	Ac		23.0-24.0/1.92-2.05
	bDGlcpN	101.7/4.61	55.8/3.77	79.9/3.78	69.6/3.69	76.8/3.48	61.7/3.75-3.90

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,2	Ac		1.92 2.05
3,6,3,5	Ac		1.92 2.05
3,6,3,7	Ac		1.92 2.05
3,6,3	bXPsep			1.66 2.53	3.86	4.19	3.87	3.98	4.11	1.21
3,6	aDGalp	4.99	3.85	4.34	4.01	3.89	3.61 3.65
3	aDGlcpN	5.36	4.08	3.76	3.68	3.75	3.69 4.03
2	Ac		1.92 2.05
	bDGlcpN	4.61	3.77	3.78	3.69	3.48	3.75 3.90

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,2	Ac	174.5 175.9	23.0 24.0
3,6,3,5	Ac	174.5 175.9	23.0 24.0
3,6,3,7	Ac	174.5 175.9	23.0 24.0
3,6,3	bXPsep	?	?	37.0	67.9	49.6	74.6	55.0	70.2	18.7
3,6	aDGalp	99.7	68.5	74.0	69.1	72.0	62.3
3	aDGlcpN	98.4	53.7	80.9	72.2	72.3	66.8
2	Ac	174.5 175.9	23.0 24.0
	bDGlcpN	101.7	55.8	79.9	69.6	76.8	61.7

The spectrum also has 2 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]O[C@H]1[C@H](O)[C@@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O[C@]3(C(=O)O)C[C@H](O)[C@H](NC(C)=O)[C@H]([C@@H](NC(C)=O)[C@H](C)O)O3)[C@H]2O)O[C@H](O[C@@H]2[C@@H](NC(C)=O)[C@H]([*])O[C@H](CO)[C@H]2O)[C@@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize