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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)

The structure was elucidated in this paper
NCBI PubMed ID: 32932700
Publication DOI: 10.3390/polym12092073
Journal NLM ID: 101545357
Publisher: Basel: MDPI
Correspondence: shjung

konkuk.ac.kr
Institutions: Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea, Department of Systems Biotechnology & Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea

Rhizobia produces different types of surface polysaccharides. Among them, cyclic β-(1→2)-D-glucan is located in the periplasmic space of rhizobia and plays an important role in the adaptation of bacteria to osmotic adaptation. Cyclic β-(1→2)-D-glucan (CG), synthesized from Sinorhiozbium meliloti 1021, has a neutral and anionic form. In the present study, we characterized the exact chemical structures of anionic CG after purification using size exclusion s (Bio-Gel P-6 and P-2) chromatography, and DEAE-Sephadex anion exchange chromatography. The exact structure of each isolated anionic CG was characterized using various analytical methods such as nuclear magnetic resonance (NMR), attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy and matrix associated laser desorption ionization-time of Flight (MALDI-TOF) mass spectrometry. The precise chemical structures of novel anionic CG molecules were elucidated by various NMR spectroscopic analyses, including 1H, 13C, 31P, and 2D HSQC NMR spectroscopy. As a result, we discovered that anionic CG molecules have either glycerophosphoryl or succinyl residues at C6 positions of a neutral CG. In addition, the results of MALDI-TOF mass spectrometric analysis confirmed that there are two types of patterns for anionic CG peaks, where one type of peak was the succinylated CG (SCG) and the other was glycerophospholated CG (GCG). In addition, it was revealed that each anionic CG has one to four substituents of the succinyl group of SCG and glycerophosphoryl group of GCG, respectively. Anionic CG could have potential as a cyclic polysaccharide for drug delivery systems and a chiral separator based on the complexation with basic target molecules.

NMR, characterization, MALDI-TOF, Sinorhizobium meliloti 1021, anionic cyclic beta-(1>2)-D-glucan, cyclic polysaccharide, phosphglycerol substituents

Structure type: cyclic polymer repeating unit ; n=19-25
Location inside paper: Fig.2, Fig.3
Trivial name: cyclic β-(1→2)-D-glucan (anionic CG)
Compound class: surface-layer polysaccharide
Contained glycoepitopes: IEDB_130695,IEDB_140628,IEDB_142488,IEDB_146664,IEDB_241118,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, anion-exchange chromatography, MALDI-TOF MS, SEC, FE-SEM, ATR-FTIR
Comments, role: Anionic glucans contains 1-4 succinyl and phosphoglycerol residues per molecule. The two substituents were not present in one molecule at the same time, but existed separately in each molecule.

NCBI Taxonomy refs (TaxIDs): 266834
Show glycosyltransferases

¹H NMR data: present in publication

¹³C NMR data: present in publication

There are 2 chemically distinct structures. Please, select:

[*]O[C@H]1[C@H]([*])O[C@H](COP(=O)(O)OCC(O)CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)

The structure was elucidated in this paper
NCBI PubMed ID: 32919551
Publication DOI: 10.1016/j.carbpol.2020.116737
Journal NLM ID: 8307156
Publisher: Elsevier
Correspondence: C. Abrusci <concepcion.abrusci

uam.es>
Institutions: Departamento de Biología Molecular, Facultad de Ciencias, Universidad Autónoma de Madrid, UAM, Cantoblanco, 28049, Madrid, Spain, Centro de Biología Molecular Severo Ochoa, CSIC-UAM, Madrid, Spain, CIC bioGUNE, Basque Research and Technology Alliance-BRTA, Parque Cientifico Tecnológico de Bizkaia, 48160, Derio, Biscay, Spain, Ikerbasque, Basque Foundation for Science, 48009, Bilbao, Biscay, Spain

The exopolymer (EPSp) produced by the strain B. licheniformis IDN-EC was isolated and characterized using different techniques (MALDI-TOF, NMR, ATR-FTIR, TGA, DSC, SEM). The results showed that the low molecular weight EPSp contained a long polyglutamic acid and an extracellular teichoic acid polysaccharide. The latter was composed of poly(glycerol phosphate) and was substituted at the 2-position of the glycerol residues with a αGal and αGlcNH2. The αGal O-6 position was also found to be substituted by a phosphate group. The antiviral capability of this EPSp was also tested on both enveloped (herpesviruses HSV, PRV and vesicular stomatitis VSV) and non-enveloped (MVM) viruses. The EPSp was efficient at inhibiting viral entry for the herpesviruses and VSV but was not effective against non-enveloped viruses. The in vivo assay of the EPSp in mice showed no signs of toxicity which could allow for its application in the healthcare sector.

teichoic acids, Bacillus licheniformis, Antiviral, Enveloped viruses, Poly(gamma-glutamic acid)

Structure type: structural motif or average structure ; 5000
Location inside paper: Fig. 3
Trivial name: extracellular teichoic acid polysaccharide (EC-TA)
Compound class: EPS
Contained glycoepitopes: IEDB_130695,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_7

Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, 31P NMR, MALDI-TOF MS, HPLC, SEM, TGA, DSC, ATR-FTIR, antiviral assay, HPLC-MS/MS
Comments, role: Proposed idealized structures of major EPS; some chains do not contain GlcpN residues.

NCBI Taxonomy refs (TaxIDs): 1402
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,0,2,0	x?Gro
2,6,0,2	%xXP?
2,6,0,3,0	x?Gro
2,6,0,3	%xXP?
2,6,0	x?Gro
2,6	P
2	aDGalp	101.2	71.0	71.8	71.6	72.5	67.3
1,0,1,0,2	aDGlcpN	99.4	56.3	73.7	72.7	74.7	63.2
1,0,1,0,1,0,1,0,2,6,0,0	x?Gro
1,0,1,0,1,0,1,0,2,6,0	%xXP?
1,0,1,0,1,0,1,0,2,6	P
1,0,1,0,1,0,1,0,2	aDGalp	101.2	71.0	71.8	71.6	72.5	67.3
1,0,1,0,1,0,1,0	x?Gro
1,0,1,0,1,0,1	P
1,0,1,0,1,0	x?Gro
1,0,1,0,1	P
1,0,1,0	x?Gro	67.8	78.4	67.8
1,0,1	P
1,0	x?Gro	68.8	72.1	68.8
1	P
	x?Gro	67.1	80.0	63.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,0,2,0	x?Gro
2,6,0,2	%xXP?
2,6,0,3,0	x?Gro
2,6,0,3	%xXP?
2,6,0	x?Gro
2,6	P
2	aDGalp	5.2	3.8	3.9	4.0	4.3	4.0
1,0,1,0,2	aDGlcpN	5.1	3.9	3.7	3.5	3.9	3.8-3.9
1,0,1,0,1,0,1,0,2,6,0,0	x?Gro
1,0,1,0,1,0,1,0,2,6,0	%xXP?
1,0,1,0,1,0,1,0,2,6	P
1,0,1,0,1,0,1,0,2	aDGalp	5.2	3.8	3.9	4.0	4.3	4.0
1,0,1,0,1,0,1,0	x?Gro
1,0,1,0,1,0,1	P
1,0,1,0,1,0	x?Gro
1,0,1,0,1	P
1,0,1,0	x?Gro	4.0	4.1	4.0
1,0,1	P
1,0	x?Gro	3.9	4.1	3.9
1	P
	x?Gro	4.0-4.1	3.9	3.8


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,6,0,2,0	x?Gro
2,6,0,2	%xXP?
2,6,0,3,0	x?Gro
2,6,0,3	%xXP?
2,6,0	x?Gro
2,6	P
2	aDGalp	101.2/5.2	71.0/3.8	71.8/3.9	71.6/4.0	72.5/4.3	67.3/4.0
1,0,1,0,2	aDGlcpN	99.4/5.1	56.3/3.9	73.7/3.7	72.7/3.5	74.7/3.9	63.2/3.8-3.9
1,0,1,0,1,0,1,0,2,6,0,0	x?Gro
1,0,1,0,1,0,1,0,2,6,0	%xXP?
1,0,1,0,1,0,1,0,2,6	P
1,0,1,0,1,0,1,0,2	aDGalp	101.2/5.2	71.0/3.8	71.8/3.9	71.6/4.0	72.5/4.3	67.3/4.0
1,0,1,0,1,0,1,0	x?Gro
1,0,1,0,1,0,1	P
1,0,1,0,1,0	x?Gro
1,0,1,0,1	P
1,0,1,0	x?Gro	67.8/4.0	78.4/4.1	67.8/4.0
1,0,1	P
1,0	x?Gro	68.8/3.9	72.1/4.1	68.8/3.9
1	P
	x?Gro	67.1/4.0-4.1	80.0/3.9	63.9/3.8

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,6,0,2,0	x?Gro
2,6,0,2	%xXP?
2,6,0,3,0	x?Gro
2,6,0,3	%xXP?
2,6,0	x?Gro
2,6	P
2	aDGalp	5.2	3.8	3.9	4.0	4.3	4.0
1,0,1,0,2	aDGlcpN	5.1	3.9	3.7	3.5	3.9	3.8 3.9
1,0,1,0,1,0,1,0,2,6,0,0	x?Gro
1,0,1,0,1,0,1,0,2,6,0	%xXP?
1,0,1,0,1,0,1,0,2,6	P
1,0,1,0,1,0,1,0,2	aDGalp	5.2	3.8	3.9	4.0	4.3	4.0
1,0,1,0,1,0,1,0	x?Gro
1,0,1,0,1,0,1	P
1,0,1,0,1,0	x?Gro
1,0,1,0,1	P
1,0,1,0	x?Gro	4.0	4.1	4.0
1,0,1	P
1,0	x?Gro	3.9	4.1	3.9
1	P
	x?Gro	4.0 4.1	3.9	3.8

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,6,0,2,0	x?Gro
2,6,0,2	%xXP?
2,6,0,3,0	x?Gro
2,6,0,3	%xXP?
2,6,0	x?Gro
2,6	P
2	aDGalp	101.2	71.0	71.8	71.6	72.5	67.3
1,0,1,0,2	aDGlcpN	99.4	56.3	73.7	72.7	74.7	63.2
1,0,1,0,1,0,1,0,2,6,0,0	x?Gro
1,0,1,0,1,0,1,0,2,6,0	%xXP?
1,0,1,0,1,0,1,0,2,6	P
1,0,1,0,1,0,1,0,2	aDGalp	101.2	71.0	71.8	71.6	72.5	67.3
1,0,1,0,1,0,1,0	x?Gro
1,0,1,0,1,0,1	P
1,0,1,0,1,0	x?Gro
1,0,1,0,1	P
1,0,1,0	x?Gro	67.8	78.4	67.8
1,0,1	P
1,0	x?Gro	68.8	72.1	68.8
1	P
	x?Gro	67.1	80.0	63.9

There is only one chemically distinct structure:

N[C@H]1[C@@H](OC(COP(=O)(O)OCC(O)COP(=O)(O)OCC(CO)O[C@H]2O[C@H](COP(=O)(O)OCC(COP(=O)(O)OCC(O)CO)OP(=O)(O)OCC(O)CO)[C@H](O)[C@H](O)[C@H]2O)COP(=O)(O)OCC(O)COP(=O)(O)OCC(CO)O[C@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC(O)CO)[C@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize