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Glycosidase-catalysed oligosaccharide synthesis: Preparation of N-acetylchitooligosaccharides using the beta-N-acetylhexosaminidase of Aspergillus oryzae
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UNSPECIFIED (1995) Glycosidase-catalysed oligosaccharide synthesis: Preparation of N-acetylchitooligosaccharides using the beta-N-acetylhexosaminidase of Aspergillus oryzae. CARBOHYDRATE RESEARCH, 279 . pp. 293-305. ISSN 0008-6215.
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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-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 (similar to 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 disaccharide 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, acts as acceptor giving tetra-N-acetylchitotetraose [GlcNAc(beta 1-4)GlcNAc(beta 1-4)GlcNAc(beta 1-4)GlcNAc]. The product mixture consisting of mono-, di-, tri-, and tetrasaccharides is conveniently separated by charcoal-Celite chromatography.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | CARBOHYDRATE RESEARCH | ||||
Publisher: | ELSEVIER SCIENCE BV | ||||
ISSN: | 0008-6215 | ||||
Official Date: | 27 December 1995 | ||||
Dates: |
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Volume: | 279 | ||||
Number of Pages: | 13 | ||||
Page Range: | pp. 293-305 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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