Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetylchitooligosaccharides using the beta-N-acetylhexosaminidase of Aspergillus oryzae

Carbohydrate Research
S SinghD H Crout

Abstract

The beta-N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D- glucopyranose (di-N-acetylchitobiose) and 2-acetamido-6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D- glucopyranose from p-nitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and 2-acetamido-2-deoxy-D-glucopyranose. The ratio of the two disaccharides is time-dependent. The ratio of (1-->4)- to (1-->6)-isomers is a maximum (approximately 9:1) at the point of disappearance of the glycosyl donor. If left to evolve, the ratio changes to 92:8 in favour of the (1-->6)-isomer. Either the (1-->4)- or the (1-->6)-isomer can be isolated by treating the appropriately enriched dissaccharide mixture with the beta-N-acetylhexosaminidase of Jack bean (Canavalia ensiformis) or the beta-N-acetylhexosaminidase of A. oryzae, respectively. Di-N-acetylchitobiose [GlcNAc(beta 1-4)GlcNAc] is an efficient donor of 2-acetamido-2-deoxy-D-glucopyranosyl units in reactions catalysed by the N-acetylhexosaminidase of A. oryzae. Di-N-acetylchitobiose itself acts as acceptor to give tri-N-acetylchitotriose [GlcNAc(beta 1-4)GlcNAc(beta 1-4)GlcNAc]. As the trisaccharide accumulates it, in turn, act...Continue Reading

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Citations

Jul 17, 1998·Current Opinion in Chemical Biology·D H Crout, G Vic
Feb 24, 2012·Journal of Agricultural and Food Chemistry·Hoang Anh NguyenClemens K Peterbauer
Jul 2, 2003·Bioscience, Biotechnology, and Biochemistry·Hikaru WatanabeYoshio Tsujisaka
May 5, 2010·Biotechnology Advances·Kristýna SlámováVladimír Kren
Apr 7, 2015·Applied Microbiology and Biotechnology·Christian NyffeneggerJørn Dalgaard Mikkelsen
Jan 24, 2012·Protein Expression and Purification·Kristýna SlámováVladimír Křen
Jul 16, 2004·Organic & Biomolecular Chemistry·Nuria AboitizJesús Jiménez-Barbero
Sep 20, 2008·Organic & Biomolecular Chemistry·Helle ChristensenHenrik Helligsø Jensen
Jan 22, 2009·Chembiochem : a European Journal of Chemical Biology·Karen J LoftSpencer J Williams
Sep 29, 2018·Food Science and Biotechnology·Sung Hoon ParkKwan-Hwa Park
Jul 2, 1998·Carbohydrate Research·V KrenK Bezouska
Apr 16, 1998·Pharmacology & Therapeutics·M HorschD M Rast
Jul 2, 1998·Carbohydrate Research·C Augé, D H Crout
Jul 17, 2018·Chemical Reviews·Liuqing WenPeng George Wang

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