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Synthesis of p-nitrophenyl sulfated disaccharides with β-d-(6-sulfo)-GlcNAc units using β-N-acetylhexosaminidase from Aspergillus oryzae in a transglycosylation reaction

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Abstract

When α-d-GlcNAc-OC6H4NO2 -p and β-d-(6-sulfo)-GlcNAc-OC6H4NO2-p (2) were used as substrates, β-N-acetylhexosaminidase from Aspergillus oryzae transferred the β-d-(6-sulfo)-GlcNAc(unit from 2 to α-d-GlcNAc-OC6H4NO2 -p to afford β-d-(6-sulfo)-GlcNAc-(1→4)-α-d-GlcNAc-OC6H4NO2-p (3) in a yield of 94% based on the amount of donor, 2, added. β-d-(6-sulfo)-GlcNAc-(1→4)-α-d-Glc-OC6H4NO2-p (4) was obtained with α-d-Glc-OC6H4NO2 -p as acceptor in a similar manner. With a reaction mixture of 2 and β-d-GlcNAc-OC6H4NO2-p (1) in a molar ratio of 6:1, the enzyme mediated the transfer of β-d-GlcNAc from 1 to 2, affording disaccharide β-d-GlcNAc-(1→4)-β-(6-sulfo)-d-GlcNAc-OC6H4NO2-p (5) in a yield of 13% based on the amount of 1 added.

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Acknowledgements

This work was partly supported by a grant-in-aid for scientific research from the National Natural Science Foundation of China (No. 30570415) and from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No.17380202).

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Correspondence to Xiaoxiong Zeng.

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Zeng, X., Sun, Y., Ye, H. et al. Synthesis of p-nitrophenyl sulfated disaccharides with β-d-(6-sulfo)-GlcNAc units using β-N-acetylhexosaminidase from Aspergillus oryzae in a transglycosylation reaction. Biotechnol Lett 29, 1105–1110 (2007). https://doi.org/10.1007/s10529-007-9366-x

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  • DOI: https://doi.org/10.1007/s10529-007-9366-x

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