Journal article

Chemoenzymatic Synthesis of Chito-oligosaccharides with Alternating N-D-Acetylglucosamine and D-Glucosamine

Rianne AG Harmsen, Berit Bjugan Aam, Jogi Madhuprakash, Anne Grethe Hamre, Ethan D Goddard-Borger, Stephen G Withers, Vincent GH Eijsink, Morten Sorlie

Biochemistry | AMER CHEMICAL SOC | Published : 2020

Abstract

Chito-oligosaccharides (CHOS) are homo- or hetero-oligomers of N-acetylglucosamine (GlcNAc, A) and d-glucosamine (GlcN, D). Production of well-defined CHOS-mixtures, or even pure CHOS, with specific lengths and sugar compositions, is of great interest since these oligosaccharides have interesting bioactivities. While direct chemical synthesis of CHOS is not straightforward, chemo-enzymatic approaches have shown some promise. We have used engineered glycoside hydrolases to catalyze oligomerization of activated DA building blocks through transglycosylation reactions. The building blocks were generated from readily available (GlcNAc)2-para-nitrophenol through deacetylation of the nonreducing en..

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