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

The β- N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4- O-(2-acetamido-2-deoxy- β-d-glucopyranosyl)-2-deoxy-d-glucopyranose (di- N-acetylchitobiose) and 2-acetamido-6- O-(2-acetamido-2-deoxy- β-d-glucopyranosyl)-2-deoxy-d-glucopyranose from p-nitrophenyl 2-aceta...

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Bibliographic Details
Published in:Carbohydrate research Vol. 279; pp. 293 - 305
Main Authors: Singh, Suddham, Packwood, John, Samuel, Christopher J., Critchley, P., Crout, David H.G.
Format: Journal Article
Language:English
Published: Netherlands Elsevier Ltd 27.12.1995
Subjects:
Aspergillus oryzae
Aspergillus oryzae - enzymology
beta-N-acetylhexosaminidase
beta-N-Acetylhexosaminidases - metabolism
Carbohydrate Conformation
Carbohydrate Sequence
Chitooligosaccharides
Disaccharides - biosynthesis
Disaccharides - chemistry
Disaccharides - metabolism
Enzymatic synthesis
enzymic synthesis
Glycosidase
glycosidases
Kinetics
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Molecular Structure
N-Acetylhexosaminidase
oligosaccharides
Oligosaccharides - biosynthesis
Oligosaccharides - chemistry
synthesis
Enzymatic synthesis
Glycosidase
N-Acetylhexosaminidase
Chitooligosaccharides
ISSN:0008-6215, 1873-426X
Online Access:Get full text
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Summary:The β- N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4- O-(2-acetamido-2-deoxy- β-d-glucopyranosyl)-2-deoxy-d-glucopyranose (di- N-acetylchitobiose) and 2-acetamido-6- O-(2-acetamido-2-deoxy- β-d-glucopyranosyl)-2-deoxy-d-glucopyranose from p-nitrophenyl 2-acetamido-2-deoxy- β-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 (∼ 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 β- N-acetylhexosaminidase of Jack bean ( Canavalia ensiformis) or the β- N-acetylhexosaminidase of A. oryzae, respectively. Di- N-acetylchitobiose [GlcNAc( β1-4)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( β1-4)GlcNAc( β1-4)GlcNAc]. As the trisaccharide accumulates it, in turn, acts as acceptor giving tetra- N-acetylchitotetraose [GlcNAc( β1-4)GlcNAc( β1-4)GlcNAc( β1-4)GlcNAc]. The product mixture consisting of mono-, di-, tri-, and tetrasaccharides is conveniently separated by charcoal-Celite chromatography.
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ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(95)00302-9