Synthesis of p-nitrophenyl sulfated disaccharides with beta-D-(6-sulfo)-GlcNAc units using beta-N-acetylhexosaminidase from Aspergillus oryzae in a transglycosylation reaction.
When alpha-D-GlcNAc-OC(6)H(4)NO(2) -p and beta-D-(6-sulfo)-GlcNAc-OC(6)H(4)NO(2)-p (2) were used as substrates, beta-N-acetylhexosaminidase from Aspergillus oryzae transferred the beta-D-(6-sulfo)-GlcNAc(unit from 2 to alpha-D-GlcNAc-OC(6)H(4)NO(2) -p to afford beta-D-(6-sulfo)-GlcNAc-(1-->4)-alpha-D-GlcNAc-OC(6)H(4)NO(2)-p (3) in a yield of 94% based on the amount of donor, 2, added. beta-D-(6-sulfo)-GlcNAc-(1-->4)-alpha-D-Glc-OC(6)H(4)NO(2)-p (4) was obtained with alpha-D-Glc-OC(6)H(4)NO(2) -p as acceptor in a similar manner. With a reaction mixture of 2 and beta-D-GlcNAc-OC(6)H(4)NO(2)-p (1) in a molar ratio of 6:1, the enzyme mediated the transfer of beta-D-GlcNAc from 1 to 2, affording disaccharide beta-D-GlcNAc-(1-->4)-beta-(6-sulfo)-D-GlcNAc-OC(6)H(4)NO(2)-p (5) in a yield of 13% based on the amount of 1 added.
Zeng
Xiaoxiong
X
Department of Biotechnology, College of Food Science and Technology, Nanjing Agricultural University, Weigang 1, Nanjing, PR China. zengxx@njau.edu.cn
Sun
Yi
Y
Ye
Hong
H
Liu
Jun
J
Uzawa
Hirotaka
H
D000117:Acetylglucosamine / Q000737:chemistry / Q000378:metabolism*; D001236:Aspergillus oryzae / Q000201:enzymology*; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry; D006031:Glycosylation; D019906:Nuclear Magnetic Resonance, Biomolecular; D013997:Time Factors; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism*
D004187:Disaccharides; D001619:beta-N-Acetylhexosaminidases; D000117:Acetylglucosamine