Synthesis of p-nitrophenyl sulfated disaccharides with beta-D-(6-sulfo)-GlcNAc units using beta-N-acetylhexosaminidase from Aspergillus oryzae in a transglycosylation reaction |
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| Authors: | Zeng Xiaoxiong Sun Yi Ye Hong Liu Jun Uzawa Hirotaka |
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| Affiliation: | (1) Department of Biotechnology, College of Food Science and Technology, Nanjing Agricultural University, Weigang 1, Nanjing, 210095, P.R. China;(2) Research Center of Advanced Bionics, National Institute of Advanced Industrial Science and Technology, Central 5, Higashi 1-1-1, Tsukuba 305-8565, Japan |
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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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| Keywords: | β -N-Acetylhexosaminidase GlcNAc-6-sulfate p-Nitrophenyl sulfated disaccharide Regioselectivity Transglycosylation |
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