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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: 8521857
Publication DOI: 10.1111/j.1432-1033.1995.899_3.x
Journal NLM ID: 0107600
Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: School of Chemistry, University of Hull, England.

A polysaccharide containing D-galactose, 2-deoxy-2-N-acetylamino-D-galactose and 3,6-dideoxy-3-N-(D-3-hydroxybutyryl)amino-D-galactose, probably corresponding to the lipopolysaccharide side chain, was obtained from an aqueous phenol extract of isolated cell walls from Acinetobacter baumannii strain O2. By means of NMR studies and chemical degradations, the repeating unit of the polymer was identified as a branched hexasaccharide of the structure shown, where Fuc3N represents 3-amino-3,6-dideoxygalactose and R represents D-3-hydroxybutyryl. Serological tests indicated that the polymer corresponded to the O2 antigen.

Lipopolysaccharide, Acinetobacter, Acinetobacter baumannii, O-specific polysaccharide, 6-dideoxy-D-galactose, 3-amino-3, 3-hydroxybutyric acid

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.903
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_134624,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_147450,IEDB_151528,IEDB_153207,IEDB_153208,IEDB_190606,IEDB_742248,IEDB_885822,SB_163,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88

Methods: methylation, NMR-2D, partial acid hydrolysis, NMR, Smith degradation
Enzymes that release or process the structure: D-hydroxybutyrate dehydrogenase

Related record ID(s): 5740
NCBI Taxonomy refs (TaxIDs): 470
Show glycosyltransferases

NMR conditions: in D2O at 343 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,4,2	Ac
6,4	bDGalpN	102.53	52.08	81.32	68.64	75.24	61.80
6,3,3,3,3	lR3HOBut	174.78	45.62	65.82	22.8
6,3,3,3	bDFucp3N	105.88	69.09	55.46	70.72	72.02	16.54
6,3,3,2	Ac
6,3,3	aDGalpN	94.12	48.97	77.86	69.49	72.51	62.11
6,3,2	Ac
6,3	bDGalpN	104.27	51.92	75.41	64.25	75.72	61.61
6	aDGalp	99.77	68.12	81.47	77.22	73.10	61.90
	bDGalp	105.48	71.53	73.40	69.58	73.13	67.48


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,4,2	Ac
6,4	bDGalpN	4.90	4.03	3.86	4.14	3.61	?
6,3,3,3,3	lR3HOBut	-	2.47	4.18	1.24
6,3,3,3	bDFucp3N	4.51	3.53	3.94	3.72	3.87	1.24
6,3,3,2	Ac
6,3,3	aDGalpN	5.10	4.41	3.85	4.21	?	?
6,3,2	Ac
6,3	bDGalpN	4.66	4.19	3.80	4.19	3.66	?
6	aDGalp	4.94	3.78	3.87	4.36	?	?
	bDGalp	4.52	3.57	3.64	4.00	?	3.87


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,4,2	Ac
6,4	bDGalpN	102.53/4.90	52.08/4.03	81.32/3.86	68.64/4.14	75.24/3.61	61.80/?
6,3,3,3,3	lR3HOBut		45.62/2.47	65.82/4.18	22.8/1.24
6,3,3,3	bDFucp3N	105.88/4.51	69.09/3.53	55.46/3.94	70.72/3.72	72.02/3.87	16.54/1.24
6,3,3,2	Ac
6,3,3	aDGalpN	94.12/5.10	48.97/4.41	77.86/3.85	69.49/4.21	72.51/?	62.11/?
6,3,2	Ac
6,3	bDGalpN	104.27/4.66	51.92/4.19	75.41/3.80	64.25/4.19	75.72/3.66	61.61/?
6	aDGalp	99.77/4.94	68.12/3.78	81.47/3.87	77.22/4.36	73.10/?	61.90/?
	bDGalp	105.48/4.52	71.53/3.57	73.40/3.64	69.58/4.00	73.13/?	67.48/3.87

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,4,2	Ac
6,4	bDGalpN	4.90	4.03	3.86	4.14	3.61	?
6,3,3,3,3	lR3HOBut		2.47	4.18	1.24
6,3,3,3	bDFucp3N	4.51	3.53	3.94	3.72	3.87	1.24
6,3,3,2	Ac
6,3,3	aDGalpN	5.10	4.41	3.85	4.21	?	?
6,3,2	Ac
6,3	bDGalpN	4.66	4.19	3.80	4.19	3.66	?
6	aDGalp	4.94	3.78	3.87	4.36	?	?
	bDGalp	4.52	3.57	3.64	4.00	?	3.87

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,4,2	Ac
6,4	bDGalpN	102.53	52.08	81.32	68.64	75.24	61.80
6,3,3,3,3	lR3HOBut	174.78	45.62	65.82	22.8
6,3,3,3	bDFucp3N	105.88	69.09	55.46	70.72	72.02	16.54
6,3,3,2	Ac
6,3,3	aDGalpN	94.12	48.97	77.86	69.49	72.51	62.11
6,3,2	Ac
6,3	bDGalpN	104.27	51.92	75.41	64.25	75.72	61.61
6	aDGalp	99.77	68.12	81.47	77.22	73.10	61.90
	bDGalp	105.48	71.53	73.40	69.58	73.13	67.48

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize