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.

Highlights

  • Many marine bacteria secrete extracellular polysaccharides, called exopolysaccharides (EPSs), which constitute an immense reservoir of novel molecules whose structure and functional properties are largely unknown

  • One example is the EPS secreted by the Gram-negative marine bacteria Vibrio alginolyticus (CNCM I-4994), which is produced on an industrial scale as an ingredient for cosmetic applications for its matifying and anti-inflammatory properties [7]

  • Composition analysis using gas-chromatography based on the trimethysilyl method on the residues obtained after complete hydrolysis of the polysaccharides revealed only two residues: galacturonic acid (GalA) and N-acetyl-glucosamine (GlcNAc) in a ratio of about 3.0:1.0 GalA:GlcNAc

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Summary

Introduction

Many marine bacteria secrete extracellular polysaccharides, called exopolysaccharides (EPSs), which constitute an immense reservoir of novel molecules whose structure and functional properties are largely unknown. The structural diversity of marine EPSs is associated with a wide range of biological and physico-chemical properties. One example is the EPS secreted by the Gram-negative marine bacteria Vibrio alginolyticus (CNCM I-4994), which is produced on an industrial scale as an ingredient for cosmetic applications for its matifying and anti-inflammatory properties [7]. This strain was isolated from deep water in the Aber Wrac’h estuary (Brittany, France). V. alginolyticus EPS (VA-EPS), which has a very original glucosaminogalactan backbone decorated with alanine and serine amino acids

Purification and Composition of the EPSs
D: GlcNAc
Preparation and Analysis of Standard Oligosaccharides
Position and Distribution of D-Alanine and D-Serine
Experimental Section
Monosaccharide Analysis
Methylation Analysis
Amino Acid Composition
Molecular Weight Determination
Acid Hydrolysis and Oligosaccharides Purification
Conclusions
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