Limits...
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.

Show MeSH

Related in: MedlinePlus

13C NMR of Vibrio alginolyticus exopolysaccharide recorded at 353 K. Inset: chemical structure of the polysaccharide.
© Copyright Policy
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4663550&req=5

marinedrugs-13-06723-f001: 13C NMR of Vibrio alginolyticus exopolysaccharide recorded at 353 K. Inset: chemical structure of the polysaccharide.

Mentions: The 13C NMR spectrum of the polysaccharide (Figure 1) showed signals at 95–105 ppm and were attributed to four anomeric carbons. Three signals were observed in the region of the methyl groups (15–25 ppm): the first corresponded to the methyl group of an acetyl group (22.68 ppm) and the two other signals (18.44 and 18.91 ppm) were attributed to methyl groups of amino acids. Eight different signals were observed in the region of the carbonyl groups between 175 and 180 ppm and likely corresponded to C6 of free uronic acids, carboxyl groups of amino acids and amide groups.


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)

13C NMR of Vibrio alginolyticus exopolysaccharide recorded at 353 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-f001: 13C NMR of Vibrio alginolyticus exopolysaccharide recorded at 353 K. Inset: chemical structure of the polysaccharide.
Mentions: The 13C NMR spectrum of the polysaccharide (Figure 1) showed signals at 95–105 ppm and were attributed to four anomeric carbons. Three signals were observed in the region of the methyl groups (15–25 ppm): the first corresponded to the methyl group of an acetyl group (22.68 ppm) and the two other signals (18.44 and 18.91 ppm) were attributed to methyl groups of amino acids. Eight different signals were observed in the region of the carbonyl groups between 175 and 180 ppm and likely corresponded to C6 of free uronic acids, carboxyl groups of amino acids and amide groups.

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