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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. Correlations between the amino acids (alanine and serine) with the carbohydrate backbone of the polysaccharide are highlighted.
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marinedrugs-13-06723-f005: 1H-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide. Correlations between the amino acids (alanine and serine) with the carbohydrate backbone of the polysaccharide are highlighted.

Mentions: The position of the amino acids on the polysaccharide and on the purified oligosaccharides was deduced from the 2D HMBC spectra. Figure 5 shows a close-up of the HMBC recorded on the polysaccharide highlighting the coupling of the H2 protons of alanine and serine to the C6 carbons involved in the amide linkages (A1-C6, A2-C6 and C-C6). Two different d-alanines were observed, the first was linked to the A1 GalA residue and the second to the C galacturonic acid residue. The d-serine was coupled only to the A2 GalA residue. Integration of the A1-H5 (4.91 ppm) and A2-H5 (4.96 ppm) protons indicated that about 65% of A residues were decorated with d-alanine and other 35% with d-serine.


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. Correlations between the amino acids (alanine and serine) with the carbohydrate backbone of the polysaccharide are highlighted.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-06723-f005: 1H-13C Heteronuclear chemical shift correlated spectrum (HMBC) of the Vibrio alginolyticus exopolysaccharide. Correlations between the amino acids (alanine and serine) with the carbohydrate backbone of the polysaccharide are highlighted.
Mentions: The position of the amino acids on the polysaccharide and on the purified oligosaccharides was deduced from the 2D HMBC spectra. Figure 5 shows a close-up of the HMBC recorded on the polysaccharide highlighting the coupling of the H2 protons of alanine and serine to the C6 carbons involved in the amide linkages (A1-C6, A2-C6 and C-C6). Two different d-alanines were observed, the first was linked to the A1 GalA residue and the second to the C galacturonic acid residue. The d-serine was coupled only to the A2 GalA residue. Integration of the A1-H5 (4.91 ppm) and A2-H5 (4.96 ppm) protons indicated that about 65% of A residues were decorated with d-alanine and other 35% with d-serine.

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