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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)

The structure was elucidated in this paper
NCBI PubMed ID: 32389651
Publication DOI: 10.1016/j.ijbiomac.2020.05.029
Journal NLM ID: 7909578
Publisher: Butterworth-Heinemann
Correspondence: qixiongzhang

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swu.edu.cn
Institutions: College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China, Department of Obstetrics and Gynecology, Southwest Hospital, Third Military Medical University, Chongqing 400038, China, College of Pharmacy, Army Medical University, Chongqing 400038, China

A novel exopolysaccharide (EPS) with high molecular weight (3.65 x 10(5) Da) and film-forming ability was produced by the strain Kosakonia sp. CCTCC M2018092. Partially acid hydrolyzed EPS (AH-EPS) with high content of fucose was prepared and exhaustively characterized. The molecular weight of AH-EPS was determined to be 3.47 x 10(4) Da. GC-MS and HPLC analyses indicated that AH-EPS is composed of L-fucose, d-glucose, D-galactose, D-glucuronic acid and pyruvic acid in the molar ratio of 2.03:1.00:1.18:0.64:0.67. Chemical and NMR analyses revealed that AH-EPS is an anionic heteropolysaccharide, with a major linkage structural motif as follows. Utilizing AH-EPS as reducing and stabilizing agent, silver nanoparticles (AH-EPS@Ag NPs) with uniform size (diameter about 20 nm) were synthesized through a green method. A hybrid film containing EPS and AH-EPS@Ag NPs was further prepared, and its antibacterial effectiveness to Staphylococcus aureus was confirmed. Taken together, this work revealed the structural characteristics of a novel fucose-rich polysaccharide, with good potential in developing new biodegradable antibacterial film.

polysaccharide, structural analysis, fucose, pharmaceutical, antibacterial, partial acid hydrolysis, Kosakonia sp.CCTCC M2018092

Structure type: structural motif or average structure ; 34700
Location inside paper: table3, Fig. 5, AH-EPS
Trivial name: AH-EPS
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151528,IEDB_151770,IEDB_151771,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_983931,SB_192,SB_7,SB_86

Methods: 13C NMR, 1H NMR, NMR-2D, methylation, partial acid hydrolysis, GC-MS, acid hydrolysis, Smith degradation, FTIR, composition analysis, HPLC, periodate oxidation, TEM, congo red analysis
Comments, role: NMR temperature was not specified; presumebly the major structure partially acid hydrolyzed EPS (AH-EPS) was to contain, two branching chains on every three repeating units. Published NMR chemical shifts of #4,4_bDGlcp C4 and C5 that seemed erroneously interchanged in the published assignment were swapped by CSDB staff.

NCBI Taxonomy refs (TaxIDs): 2492396
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,4	bDGlcp	102.51	76.56	81.63	71.42	76.29	62.08
4	aLFucp	101.00	73.16	72.29	79.80	67.41	15.49
3,3,3,6	x?Pyr	176.36	102.4	25.04
3,3,3	aDGalp	93.11	72.47	72.67	78.78	67.17	69.31
3,3	aDGlcpA	93.91	74.26	78.90	72.96	72.69	175.99
3	aDGalp	99.35	67.62	78.85	70.61	72.90	61.21
	aLFucp	99.25	71.22	79.96	79.80	67.41	15.32


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4	bDGlcp	4.50	3.37	3.56	3.45	3.71	3.89-3.96
4	aLFucp	4.99	4.05	3.86	3.87	4.42	1.27
3,3,3,6	x?Pyr	-	-	1.45
3,3,3	aDGalp	5.35	3.84	3.86	4.18	4.48	4.07
3,3	aDGlcpA	5.17	3.64	3.87	4.06	4.17	-
3	aDGalp	5.40	3.97	4.16	4.22	4.04	3.86
	aLFucp	5.35	3.71	3.89	3.87	4.61	1.27


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4,4	bDGlcp	102.51/4.50	76.56/3.37	81.63/3.56	71.42/3.45	76.29/3.71	62.08/3.89-3.96
4	aLFucp	101.00/4.99	73.16/4.05	72.29/3.86	79.80/3.87	67.41/4.42	15.49/1.27
3,3,3,6	x?Pyr			25.04/1.45
3,3,3	aDGalp	93.11/5.35	72.47/3.84	72.67/3.86	78.78/4.18	67.17/4.48	69.31/4.07
3,3	aDGlcpA	93.91/5.17	74.26/3.64	78.90/3.87	72.96/4.06	72.69/4.17	
3	aDGalp	99.35/5.40	67.62/3.97	78.85/4.16	70.61/4.22	72.90/4.04	61.21/3.86
	aLFucp	99.25/5.35	71.22/3.71	79.96/3.89	79.80/3.87	67.41/4.61	15.32/1.27

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
4,4	bDGlcp	4.50	3.37	3.56	3.45	3.71	3.89 3.96
4	aLFucp	4.99	4.05	3.86	3.87	4.42	1.27
3,3,3,6	x?Pyr			1.45
3,3,3	aDGalp	5.35	3.84	3.86	4.18	4.48	4.07
3,3	aDGlcpA	5.17	3.64	3.87	4.06	4.17
3	aDGalp	5.40	3.97	4.16	4.22	4.04	3.86
	aLFucp	5.35	3.71	3.89	3.87	4.61	1.27

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
4,4	bDGlcp	102.51	76.56	81.63	71.42	76.29	62.08
4	aLFucp	101.00	73.16	72.29	79.80	67.41	15.49
3,3,3,6	x?Pyr	176.36	102.4	25.04
3,3,3	aDGalp	93.11	72.47	72.67	78.78	67.17	69.31
3,3	aDGlcpA	93.91	74.26	78.90	72.96	72.69	175.99
3	aDGalp	99.35	67.62	78.85	70.61	72.90	61.21
	aLFucp	99.25	71.22	79.96	79.80	67.41	15.32

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](C)O[C@@H](O[C@@H]3[C@H](C)O[C@@H]([*])[C@@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@H](O)[C@H](O[C@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O[C@H]5O[C@@H]6COC(C)(C(=O)O)O[C@@H]6[C@H](O)[C@H]5O)[C@H]4O)[C@H]3O)[C@@H](O)[C@@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize