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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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Related in: MedlinePlus

Size-exclusion chromatogram of the acid-hydrolyzed Vibrio alginolyticus exopolysaccharide. The two main products, DP4 and DP8, are indicated.
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marinedrugs-13-06723-f004: Size-exclusion chromatogram of the acid-hydrolyzed Vibrio alginolyticus exopolysaccharide. The two main products, DP4 and DP8, are indicated.

Mentions: After mild acid hydrolysis, the degradation of the EPS was monitored by SEC (Figure 4). After 20 min in 1 M TFA at 100 °C, degradation led to three main peaks centered at 130 min (shoulder), 140 min and 160 min elution times. 1H NMR of the fractions collected at elution times of 150–165 min is given in Figure 2. The spectra showed all the characteristic signals of the polysaccharide, along with additional signals attributed to the reducing and non-reducing ends of the oligosaccharide. The signal of D-H1 (polymer) at 4.77 ppm shifted to 4.73 ppm for D-H1β (DP4). A new D-H1α signal appeared at 5.18 ppm indicating that cleavage occurred at the reducing end of the D residues. The C-H1 (polymer) at 5.43 ppm was split into two doublet signals at 5.48 ppm and 5.51 ppm (DP4). This observation suggested the α-galacturonic residue C was linked to the β-GlcNAc (D) and that the splitting distinguished C(α) from C(β) residues linked to the β- or α-GlcNAc residues, respectively. 1H/13C HMBC showed the correlation between D-C3 (α/β) (80.37 ppm/81.89 ppm) and C-H1 (Dα/β) (5.48 ppm/5.51 ppm), confirming that residue C is linked to the reducing end of β-GlcNAc (D) via an α(1,3) linkage.


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)

Size-exclusion chromatogram of the acid-hydrolyzed Vibrio alginolyticus exopolysaccharide. The two main products, DP4 and DP8, are indicated.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-06723-f004: Size-exclusion chromatogram of the acid-hydrolyzed Vibrio alginolyticus exopolysaccharide. The two main products, DP4 and DP8, are indicated.
Mentions: After mild acid hydrolysis, the degradation of the EPS was monitored by SEC (Figure 4). After 20 min in 1 M TFA at 100 °C, degradation led to three main peaks centered at 130 min (shoulder), 140 min and 160 min elution times. 1H NMR of the fractions collected at elution times of 150–165 min is given in Figure 2. The spectra showed all the characteristic signals of the polysaccharide, along with additional signals attributed to the reducing and non-reducing ends of the oligosaccharide. The signal of D-H1 (polymer) at 4.77 ppm shifted to 4.73 ppm for D-H1β (DP4). A new D-H1α signal appeared at 5.18 ppm indicating that cleavage occurred at the reducing end of the D residues. The C-H1 (polymer) at 5.43 ppm was split into two doublet signals at 5.48 ppm and 5.51 ppm (DP4). This observation suggested the α-galacturonic residue C was linked to the β-GlcNAc (D) and that the splitting distinguished C(α) from C(β) residues linked to the β- or α-GlcNAc residues, respectively. 1H/13C HMBC showed the correlation between D-C3 (α/β) (80.37 ppm/81.89 ppm) and C-H1 (Dα/β) (5.48 ppm/5.51 ppm), confirming that residue C is linked to the reducing end of β-GlcNAc (D) via an α(1,3) linkage.

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