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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-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide (A) and its oligosaccharides: DP4 (B) and DP8 (C). Correlations demonstrating the linkages between residues in the repetition moieties are indicated.
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marinedrugs-13-06723-f003: 1H-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide (A) and its oligosaccharides: DP4 (B) and DP8 (C). Correlations demonstrating the linkages between residues in the repetition moieties are indicated.

Mentions: HMBC experiments to analyze the 1H/13C heterenuclear coupling relationships highlighted linkage between most of the residues (Figure 3A). The A-C3 carbon (78.97 ppm) was coupled to the D-H1 proton (4.77 ppm), indicating that the β-d-GlcNAc (D) residue is linked to the α-d-GalA (A) residue via a β(1,3) linkage. Similarly, the correlation between B-C4 (78.68/78.85 ppm) and A-H1 (5.18/5.19 ppm) suggested that the linkage between the two α-d-GalA residues A and B occurs through an α(1,4) linkage. The linkage between the two α-d-GalA residues B and C was also demonstrated (correlations C-C3: 76.06/B-H1: 5.22 ppm and B-C1: 97.20/C-H3: 4.03 ppm) and B is linked to C via an α(1,3) linkage. The linkage between the α-d-GalA residue C with the β-GlcNAc (D) could not be determined here.


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-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide (A) and its oligosaccharides: DP4 (B) and DP8 (C). Correlations demonstrating the linkages between residues in the repetition moieties are indicated.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-06723-f003: 1H-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide (A) and its oligosaccharides: DP4 (B) and DP8 (C). Correlations demonstrating the linkages between residues in the repetition moieties are indicated.
Mentions: HMBC experiments to analyze the 1H/13C heterenuclear coupling relationships highlighted linkage between most of the residues (Figure 3A). The A-C3 carbon (78.97 ppm) was coupled to the D-H1 proton (4.77 ppm), indicating that the β-d-GlcNAc (D) residue is linked to the α-d-GalA (A) residue via a β(1,3) linkage. Similarly, the correlation between B-C4 (78.68/78.85 ppm) and A-H1 (5.18/5.19 ppm) suggested that the linkage between the two α-d-GalA residues A and B occurs through an α(1,4) linkage. The linkage between the two α-d-GalA residues B and C was also demonstrated (correlations C-C3: 76.06/B-H1: 5.22 ppm and B-C1: 97.20/C-H3: 4.03 ppm) and B is linked to C via an α(1,3) linkage. The linkage between the α-d-GalA residue C with the β-GlcNAc (D) could not be determined here.

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