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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cholera [ICD11: 1A00

, ICD11: XN7N1

]

The structure was elucidated in this paper
NCBI PubMed ID: 30530139
Publication DOI: 10.1016/j.carres.2018.11.001
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: A.V. Perepelov <andreivperepelov

gmail.com>
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institure of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China

O-polysaccharide (O-antigen) was isolated from the lipopolysaccharide of Vibrio cholerae O100 and studied by component analyses and 1D and 2D NMR spectroscopy. The following structure of the O-polysaccharide was established: →3)-β-d-QuipNAc4N(dHh)-(1→3)-α-d-Fucp4N(RHb)-(1→3)-α-l-FucpNAc-( 1→ where Hb and dHh indicate 3-hydroxybutanoyl and 3,5-dihydroxyhexanoyl, respectively. The O-antigen gene cluster of V. cholerae O100 has been sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in agreement with the OPS structure.

Lipopolysaccharide, O-antigen, O-specific polysaccharide, bacterial polysaccharide structure, Vibrio cholerae, O-antigen gene cluster

Structure type: polymer chemical repeating unit
Location inside paper: abstract, table 1, p.100
The structure in this paper was incorrect:

Original structure from CSDB record 1088

← originally published structure

Show legend

Compound class: O-polysaccharide, O-antigen

Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, acid hydrolysis, GLC, GPC, function analysis of gene clusters
Comments, role: V. cholerae O100 type strain (laboratory stock number G5610). Error in the OPS structure presented on page 100. Published erroneous NMR chemical shift of #_aLFucpN C4 (54.2) was corrected by CSDB staff based on a spectrum figure. Published erroneous NMR chemical shifts of #_aLFucpN C5 (67.2), #3_aDFucp4N C5 (67.2), #_aLFucpN H2 (3.71) and H5 (4.19), and #3_aDFucp4N H2 (3.71) and H5 (4.19) were removed by CSDB staff.

NCBI Taxonomy refs (TaxIDs): 666
Show glycosyltransferases

NMR conditions: in D2O / H2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	Ac	174.9-175.8	23.4-23.7
3,3,4	lX3,5HOHex	175.5	45.2	67.9	46.3	66.2	23.1
3,3	bDQuipN4N	102.8	57.5	76.3	56.7	71.9	18.3
3,4	lR3HOBut	175.7	46.0	66.3	23.2
3	aDFucp4N	102.3	69.2	77.7	54.2	?	16.8
2	Ac	174.9-175.8	23.4-23.7
	aLFucpN	98.3	48.9	77.5	72	?	16.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	Ac	-	1.92-2.00
3,3,4	lX3,5HOHex	-	2.39	4.12	1.59-1.73	3.96	1.19
3,3	bDQuipN4N	4.62	3.87	3.76	3.71	3.55	1.21
3,4	lR3HOBut	-	2.47	4.18	1.26
3	aDFucp4N	4.94	?	4.04	4.35	?	1.06
2	Ac	-	1.92-2.00
	aLFucpN	5.08	?	3.72	4.35	?	1.06


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,2	Ac		23.4-23.7/1.92-2.00
3,3,4	lX3,5HOHex		45.2/2.39	67.9/4.12	46.3/1.59-1.73	66.2/3.96	23.1/1.19
3,3	bDQuipN4N	102.8/4.62	57.5/3.87	76.3/3.76	56.7/3.71	71.9/3.55	18.3/1.21
3,4	lR3HOBut		46.0/2.47	66.3/4.18	23.2/1.26
3	aDFucp4N	102.3/4.94	69.2/?	77.7/4.04	54.2/4.35	?/?	16.8/1.06
2	Ac		23.4-23.7/1.92-2.00
	aLFucpN	98.3/5.08	48.9/?	77.5/3.72	72/4.35	?/?	16.8/1.06

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	Ac		1.92 2.00
3,3,4	lX3,5HOHex		2.39	4.12	1.59 1.73	3.96	1.19
3,3	bDQuipN4N	4.62	3.87	3.76	3.71	3.55	1.21
3,4	lR3HOBut		2.47	4.18	1.26
3	aDFucp4N	4.94	?	4.04	4.35	?	1.06
2	Ac		1.92 2.00
	aLFucpN	5.08	?	3.72	4.35	?	1.06

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	Ac	174.9 175.8	23.4 23.7
3,3,4	lX3,5HOHex	175.5	45.2	67.9	46.3	66.2	23.1
3,3	bDQuipN4N	102.8	57.5	76.3	56.7	71.9	18.3
3,4	lR3HOBut	175.7	46.0	66.3	23.2
3	aDFucp4N	102.3	69.2	77.7	54.2	?	16.8
2	Ac	174.9 175.8	23.4 23.7
	aLFucpN	98.3	48.9	77.5	72	?	16.8

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

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize