@article {queda2019top, title = {A top-down chemo-enzymatic approach towards N-acetylglucosamine-N-acetylmuramic oligosaccharides: Chitosan as a reliable template}, journal = {Carbohydrate Polymers}, volume = {224}, year = {2019}, note = {

n/a

}, pages = {115133}, publisher = {Elsevier}, 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 {\textendash} biologically important targets.

}, url = {https://www.sciencedirect.com/science/article/pii/S0144861719308008}, author = {Queda, Fausto and Covas, Gon{\c c}alo and Silva, Tom{\'e} and Santos, C{\'a}tia Almeida and Bronze, Maria R. and Ca{\~n}ada, Francisco Javier and Corvo, Marta C. and Filipe, S{\'e}rgio R and Marques, M. Manuel B.} }