A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template. (15th November 2019)

• Record Type: Journal Article
• Authors: Queda, Fausto; Covas, Gonçalo; Silva, Tomé; Santos, Cátia Almeida; Bronze, Maria R.; Cañada, Francisco Javier; Corvo, Marta C.; Filipe, Sérgio R.; Marques, M. Manuel B.
• Is Part Of: Carbohydrate polymers. Volume 224(2019)
• Publication Date: 2019-11-15
• Subjects: Chitosan -- Chitooligosaccharides -- Chemo-enzymatic -- Regioselective modification; Polysaccharides -- Periodicals; Polysaccharides -- Periodicals; Polysaccharides -- Périodiques; Electronic journals; 547.78
• DOI: 10.1016/j.carbpol.2019.115133
• Languages: English
• ISSNs: 0144-8617

Abstract

Graphical abstract: Highlights: A novel and simple approach towards NAG-NAM surrogates was developed. First chemo and enzymatic route to produce NAG-NAM oligosaccharides from chitosan. Production of an oligosaccharide containing NAG-NAM from chitosan in 33% yield. NAG-NAM oligosaccharides are relevant surrogates recognized by enzymes. Isolated products are valuable materials to study bacterial infections. Abstract: An unprecedented approach towards oligosaccharides containing N -acetylglucosamine- N -acetylmuramic (NAG-NAM) units was developed. These novel bacterial cell wall surrogates were obtained from chitosan via a top down approach involving both chemical and enzymatic reactions. The chemical modification of chitosan using a molecular clamp based strategy, allowed obtaining N -acetylglucosamine- N -acetylmuramic (NAG-NAM) containing oligomers. Intercalation of NAM residues was confirmed through the analysis of oligosaccharide fragments from enzymatic digestion and it was found that this route affords NAG-NAM containing oligosaccharides in 33% yield. These oligosaccharides mimic the carbohydrate basic skeleton of most bacterial cell surfaces. The oligosaccharides prepared are biologically relevant and will serve as a platform for further molecular recognition studies with different receptors and enzymes of both bacterial cell wall and innate immune system. This strategy combining both chemical modification and enzymatic digestion provides a novel and simple route for an easy access to bacterial cell wall fragments – biologically important targets.