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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Veröffentlicht in:	Carbohydrate research Jg. 279; S. 293 - 305
Hauptverfasser:	Singh, Suddham, Packwood, John, Samuel, Christopher J., Critchley, P., Crout, David H.G.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Netherlands Elsevier Ltd 27.12.1995
Schlagworte:	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
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Abstract	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.
AbstractList	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 leads to 4)- to (1 leads to 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 leads to 6)-isomer. Either the (1 leads to 4)- or the (1 leads to 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 leads to 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 leads to 4)GlcNAc (beta 1 leads to 4)GlcNAc]. As the trisaccharide accumulates it, in turn, acts as acceptor giving tetra-N-acetylchitotetraose [GlcNAc(beta 1 leads to 4)GlcNAc(beta 1 leads to 4)GlcNAc(beta 1 leads to 4)GlcNAc]. The product mixture consisting of mono-, di-, tri, and tetrasaccharides is conveniently separated by charcoal-Celite chromatography. 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, 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. 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, 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.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, 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. 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.
Author	Samuel, Christopher J. Crout, David H.G. Critchley, P. Singh, Suddham Packwood, John
Author_xml	– sequence: 1 givenname: Suddham surname: Singh fullname: Singh, Suddham – sequence: 2 givenname: John surname: Packwood fullname: Packwood, John – sequence: 3 givenname: Christopher J. surname: Samuel fullname: Samuel, Christopher J. – sequence: 4 givenname: P. surname: Critchley fullname: Critchley, P. – sequence: 5 givenname: David H.G. surname: Crout fullname: Crout, David H.G.
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Keywords	Enzymatic synthesis Glycosidase N-Acetylhexosaminidase Chitooligosaccharides
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Snippet	The β- N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4- O-(2-acetamido-2-deoxy-... The beta-N-acetylhexosaminidase of Aspergillus oryzae catalyses the formation of 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D... 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-...
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SubjectTerms	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
Title	Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetylchitooligosaccharides using the β- N-acetylhexosaminidase of Aspergillus oryzae
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