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Structure of an Amino Acid-Decorated Exopolysaccharide Secreted by a Vibrio alginolyticus Strain.

Drouillard S, Jeacomine I, Buon L, Boisset C, Courtois A, Thollas B, Morvan PY, Vallée R, Helbert W - Mar Drugs (2015)

Bottom Line: The results show that the carbohydrate backbone is made of two residues: d-galacturonic acid and N-acetyl-d-glucosamine (GlcNac), which together constitute a tetrasaccharide repetition unit: [→3)-α-d-GalA-(1→4)-α-d-GalA-(1→3)-α-d-GalA-(1→3)-β-GlcNAc(1→].Two amino acids, alanine and serine, are linked to GalA residues via amido linkages.To our knowledge, this is the first description of a structure for a marine exopolysaccharide decorated with an amino acid.

View Article: PubMed Central - PubMed

Affiliation: Université Grenoble Alpes, CERMAV, CNRS, 38000 Grenoble, France. sophie.drouillard@cermav.cnrs.fr.

ABSTRACT
Vibrio alginolyticus (CNCM I-4994) secretes an exopolysaccharide that can be used as an ingredient in cosmetic applications. The structure was resolved using chromatography and one- and two-dimensional NMR spectroscopy experiments. The results show that the carbohydrate backbone is made of two residues: d-galacturonic acid and N-acetyl-d-glucosamine (GlcNac), which together constitute a tetrasaccharide repetition unit: [→3)-α-d-GalA-(1→4)-α-d-GalA-(1→3)-α-d-GalA-(1→3)-β-GlcNAc(1→]. Two amino acids, alanine and serine, are linked to GalA residues via amido linkages. The position and the distribution of the amino acids were characterized by two-dimensional NMR spectroscopy. To our knowledge, this is the first description of a structure for a marine exopolysaccharide decorated with an amino acid.

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1H NMR of the Vibrio alginolyticus exopolysaccharide and its oligosaccharides (DP4, DP8) purified after acid hydrolysis. (A) The 1H NMR of the polysaccharide was recorded at 353 K; (B,C) 1H NMR of DP4 and DP8, respectively, recorded at 293 K. Inset: chemical structure of the polysaccharide.
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marinedrugs-13-06723-f002: 1H NMR of the Vibrio alginolyticus exopolysaccharide and its oligosaccharides (DP4, DP8) purified after acid hydrolysis. (A) The 1H NMR of the polysaccharide was recorded at 353 K; (B,C) 1H NMR of DP4 and DP8, respectively, recorded at 293 K. Inset: chemical structure of the polysaccharide.

Mentions: Inspection of 1H NMR spectra (Figure 2) and 1H/13C heteronuclear single-quantum correlations (HSQC) of the EPS (not shown) confirmed a repetition unit made of four distinct residues of which three (A–C) adopt an α-anomeric configuration and the fourth (D) has a β-anomeric configuration. 1H NMR spectra confirmed that the repetition moiety is a tetrasaccharide decorated with N-acetyl groups and amino acids.


Structure of an Amino Acid-Decorated Exopolysaccharide Secreted by a Vibrio alginolyticus Strain.

Drouillard S, Jeacomine I, Buon L, Boisset C, Courtois A, Thollas B, Morvan PY, Vallée R, Helbert W - Mar Drugs (2015)

1H NMR of the Vibrio alginolyticus exopolysaccharide and its oligosaccharides (DP4, DP8) purified after acid hydrolysis. (A) The 1H NMR of the polysaccharide was recorded at 353 K; (B,C) 1H NMR of DP4 and DP8, respectively, recorded at 293 K. Inset: chemical structure of the polysaccharide.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4663550&req=5

marinedrugs-13-06723-f002: 1H NMR of the Vibrio alginolyticus exopolysaccharide and its oligosaccharides (DP4, DP8) purified after acid hydrolysis. (A) The 1H NMR of the polysaccharide was recorded at 353 K; (B,C) 1H NMR of DP4 and DP8, respectively, recorded at 293 K. Inset: chemical structure of the polysaccharide.
Mentions: Inspection of 1H NMR spectra (Figure 2) and 1H/13C heteronuclear single-quantum correlations (HSQC) of the EPS (not shown) confirmed a repetition unit made of four distinct residues of which three (A–C) adopt an α-anomeric configuration and the fourth (D) has a β-anomeric configuration. 1H NMR spectra confirmed that the repetition moiety is a tetrasaccharide decorated with N-acetyl groups and amino acids.

Bottom Line: The results show that the carbohydrate backbone is made of two residues: d-galacturonic acid and N-acetyl-d-glucosamine (GlcNac), which together constitute a tetrasaccharide repetition unit: [→3)-α-d-GalA-(1→4)-α-d-GalA-(1→3)-α-d-GalA-(1→3)-β-GlcNAc(1→].Two amino acids, alanine and serine, are linked to GalA residues via amido linkages.To our knowledge, this is the first description of a structure for a marine exopolysaccharide decorated with an amino acid.

View Article: PubMed Central - PubMed

Affiliation: Université Grenoble Alpes, CERMAV, CNRS, 38000 Grenoble, France. sophie.drouillard@cermav.cnrs.fr.

ABSTRACT
Vibrio alginolyticus (CNCM I-4994) secretes an exopolysaccharide that can be used as an ingredient in cosmetic applications. The structure was resolved using chromatography and one- and two-dimensional NMR spectroscopy experiments. The results show that the carbohydrate backbone is made of two residues: d-galacturonic acid and N-acetyl-d-glucosamine (GlcNac), which together constitute a tetrasaccharide repetition unit: [→3)-α-d-GalA-(1→4)-α-d-GalA-(1→3)-α-d-GalA-(1→3)-β-GlcNAc(1→]. Two amino acids, alanine and serine, are linked to GalA residues via amido linkages. The position and the distribution of the amino acids were characterized by two-dimensional NMR spectroscopy. To our knowledge, this is the first description of a structure for a marine exopolysaccharide decorated with an amino acid.

Show MeSH
Related in: MedlinePlus