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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: 31220143
Publication DOI: 10.1371/journal.pone.0218461
Journal NLM ID: 101285081
Publisher: San Francisco, CA: Public Library of Science
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, 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, Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia.4 Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia

Acinetobacter baumannii isolate NIPH 329 carries a novel capsular polysaccharide (CPS) gene cluster, designated KL46, that is closely related to the KL5 locus in A. baumannii isolate SDF but includes genes for synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic (di-N-acetylpseudaminic) acid (Pse5Ac7Ac) instead of the corresponding D-glycero-D-galacto isomer (di-N-acetyllegionaminic acid) (Leg5Ac7Ac). In agreement with the genetic content of KL46, chemical studies of the K46 CPS produced by NIPH 329 revealed a branched tetrasaccharide repeat (K unit) with an overall structure the same as K5 from SDF but with β-Pse5Ac7Ac replacing α-Leg5Ac7Ac. As for K5, the K46 unit begins with d-GalpNAc and includes α-d-GlcpNAc-(1→3)-d-GalpNAc and α-d-Galp-(1→6)-d-GlcpNAc linkages, formed by Gtr14 and Gtr15 glycosyltransferases, respectively. The Gtr94K46 glycosyltransferase, which is related to Gtr13K5, links Pse5Ac7Ac to d-Galp in the growing K unit via a β-(2→6) linkage. Nearly identical Wzy enzymes connect the K46 and K5 units via a α-D-GalpNAc-(1→3)-α-D-Galp linkage to form closely related CPSs. Both Pse5Ac7Ac in K46 and Leg5Ac7Ac in K5 are acetylated at O4 but no acetyltransferase gene is present in KL46 or KL5. Related acetyltransferases were found encoded in the NIPH 329 and SDF genomes, but not in other strains carrying an unacetylated Pse or Leg derivative in the CPS. The genes encoding the acetyltransferases were in different putative phage genomes. However, related acetyltransferases were rare among the >3000 publically available genome sequences.

biosynthesis, capsular polysaccharide, locus, Acinetobacter baumannii, gene cluster, nonulosonic acid, glycosyltransferase

Structure type: polymer chemical repeating unit
Location inside paper: table 1, fig.2, , fig.4A, K46
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_838988,SB_21,SB_7

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, GLC, mild acid hydrolysis, Smith degradation, GPC, bioinformatic analysis
Enzymes that release or process the structure: Gtr94, Gtr14, Gtr15 glycosyltransferases, Wzy(K46)[ItrA2]
Biosynthesis and genetic data: genetic data

Related record ID(s): 1365, 1366, 1367, 1368
NCBI Taxonomy refs (TaxIDs): 1217632
Reference(s) to other database(s): GTC:G90220UD
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,6,6,4	75%Ac	174.1	21.7
3,6,6,5	Ac	174.5-175.9	23.0-24.0
3,6,6,7	Ac	174.5-175.9	23.0-24.0
3,6,6	bXPsep	173.3	101.5	33.8	70.1	47.0	74.0	54.8	69.5	17.8
3,6	aDGalp	99.7	68.7	80.6	70.5	70.5	65.2
3,2	Ac	174.5-175.9	23.0-24.0
3	aDGlcpN	95.6	54.6	72.5	70.4	72.6	66.2
2	Ac	174.5-175.9	23.0-24.0
	bDGalpN	103.9	52.4	77.0	65.4	76.1	62.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,6,6,4	75%Ac	-	2.00
3,6,6,5	Ac	-	1.92-2.05
3,6,6,7	Ac	-	1.92-2.05
3,6,6	bXPsep	-	-	1.76-2.50	4.90	4.30	4.00	4.07	4.13	1.19
3,6	aDGalp	4.97	3.92	3.95	4.21	4.05	3.58-3.95
3,2	Ac	-	1.92-2.05
3	aDGlcpN	5.05	3.96	3.65	3.74	3.73	3.64-4.16
2	Ac	-	1.92-2.05
	bDGalpN	4.71	4.07	3.82	4.07	3.62	3.74-3.79


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
3,6,6,4	75%Ac		21.7/2.00
3,6,6,5	Ac		23.0-24.0/1.92-2.05
3,6,6,7	Ac		23.0-24.0/1.92-2.05
3,6,6	bXPsep			33.8/1.76-2.50	70.1/4.90	47.0/4.30	74.0/4.00	54.8/4.07	69.5/4.13	17.8/1.19
3,6	aDGalp	99.7/4.97	68.7/3.92	80.6/3.95	70.5/4.21	70.5/4.05	65.2/3.58-3.95
3,2	Ac		23.0-24.0/1.92-2.05
3	aDGlcpN	95.6/5.05	54.6/3.96	72.5/3.65	70.4/3.74	72.6/3.73	66.2/3.64-4.16
2	Ac		23.0-24.0/1.92-2.05
	bDGalpN	103.9/4.71	52.4/4.07	77.0/3.82	65.4/4.07	76.1/3.62	62.4/3.74-3.79

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
3,6,6,4	75%Ac		2.00
3,6,6,5	Ac		1.92 2.05
3,6,6,7	Ac		1.92 2.05
3,6,6	bXPsep			1.76 2.50	4.90	4.30	4.00	4.07	4.13	1.19
3,6	aDGalp	4.97	3.92	3.95	4.21	4.05	3.58 3.95
3,2	Ac		1.92 2.05
3	aDGlcpN	5.05	3.96	3.65	3.74	3.73	3.64 4.16
2	Ac		1.92 2.05
	bDGalpN	4.71	4.07	3.82	4.07	3.62	3.74 3.79

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
3,6,6,4	75%Ac	174.1	21.7
3,6,6,5	Ac	174.5 175.9	23.0 24.0
3,6,6,7	Ac	174.5 175.9	23.0 24.0
3,6,6	bXPsep	173.3	101.5	33.8	70.1	47.0	74.0	54.8	69.5	17.8
3,6	aDGalp	99.7	68.7	80.6	70.5	70.5	65.2
3,2	Ac	174.5 175.9	23.0 24.0
3	aDGlcpN	95.6	54.6	72.5	70.4	72.6	66.2
2	Ac	174.5 175.9	23.0 24.0
	bDGalpN	103.9	52.4	77.0	65.4	76.1	62.4

There is only one chemically distinct structure:

[*]O[C@@H]1[C@@H](O)[C@@H](OC[C@H]2O[C@H](O[C@@H]3[C@@H](NC(C)=O)[C@H]([*])O[C@H](CO)[C@@H]3O)[C@H](NC(C)=O)[C@@H](O)[C@@H]2O)O[C@H](CO[C@]2(C(=O)O)C[C@H](OC(C)=O)[C@H](NC(C)=O)[C@H]([C@@H](NC(C)=O)[C@H](C)O)O2)[C@@H]1O

SVG MW SMILES 3D mol Ionize