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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: 35872312
Publication DOI: 10.1016/j.ijbiomac.2022.07.136
Journal NLM ID: 7909578
Publisher: 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
Location inside paper: p. 451, table 1, p. 452, Fig. 5A, MPS
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
Comments, role: Structure of a modified polysaccharide MPS (depyruvylated CPS)

Related record ID(s): 8486, 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	175.2-176.1	23.4-23.9
3,4,6	aDGalpN	98.6	49.7	77.8	69.8	71.9	62.5
3,4,2	Ac	175.2-176.1	23.4-23.9
3,4	aDGlcpN	100.1	55.1	72.2	71.1	72.5	66.5
3,2	Ac	175.2-176.1	23.4-23.9
3	aDGalpNA	99.7	50.8	68.0	79.6	71.9	173.6
2	Ac	175.2-176.1	23.4-23.9
	bDQuipN	103.1	55.8	81.6	77.6	72.9	18.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,6,2	Ac	-	1.93-2.07
3,4,6	aDGalpN	4.90	4.27	3.95	4.18	3.97	3.73
3,4,2	Ac	-	1.93-2.07
3,4	aDGlcpN	4.92	3.91	3.79	3.60	4.22	3.58-3.99
3,2	Ac	-	1.93-2.07
3	aDGalpNA	5.36	4.24	3.99	4.38	4.31	-
2	Ac	-	1.93-2.07
	bDQuipN	4.59	3.77	3.67	3.39	3.46	1.28


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,6,2	Ac		23.4-23.9/1.93-2.07
3,4,6	aDGalpN	98.6/4.90	49.7/4.27	77.8/3.95	69.8/4.18	71.9/3.97	62.5/3.73
3,4,2	Ac		23.4-23.9/1.93-2.07
3,4	aDGlcpN	100.1/4.92	55.1/3.91	72.2/3.79	71.1/3.60	72.5/4.22	66.5/3.58-3.99
3,2	Ac		23.4-23.9/1.93-2.07
3	aDGalpNA	99.7/5.36	50.8/4.24	68.0/3.99	79.6/4.38	71.9/4.31	
2	Ac		23.4-23.9/1.93-2.07
	bDQuipN	103.1/4.59	55.8/3.77	81.6/3.67	77.6/3.39	72.9/3.46	18.0/1.28

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,6,2	Ac		1.93 2.07
3,4,6	aDGalpN	4.90	4.27	3.95	4.18	3.97	3.73
3,4,2	Ac		1.93 2.07
3,4	aDGlcpN	4.92	3.91	3.79	3.60	4.22	3.58 3.99
3,2	Ac		1.93 2.07
3	aDGalpNA	5.36	4.24	3.99	4.38	4.31
2	Ac		1.93 2.07
	bDQuipN	4.59	3.77	3.67	3.39	3.46	1.28

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,6,2	Ac	175.2 176.1	23.4 23.9
3,4,6	aDGalpN	98.6	49.7	77.8	69.8	71.9	62.5
3,4,2	Ac	175.2 176.1	23.4 23.9
3,4	aDGlcpN	100.1	55.1	72.2	71.1	72.5	66.5
3,2	Ac	175.2 176.1	23.4 23.9
3	aDGalpNA	99.7	50.8	68.0	79.6	71.9	173.6
2	Ac	175.2 176.1	23.4 23.9
	bDQuipN	103.1	55.8	81.6	77.6	72.9	18.0

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize