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

Biotechnol Lett. 2007 Jul;29(7):1105-10. doi: 10.1007/s10529-007-9366-x. Epub 2007 May 11.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry
  • Acetylglucosamine / metabolism*
  • Aspergillus oryzae / enzymology*
  • Disaccharides / biosynthesis*
  • Disaccharides / chemistry
  • Glycosylation
  • Nuclear Magnetic Resonance, Biomolecular
  • Time Factors
  • beta-N-Acetylhexosaminidases / metabolism*

Substances

  • Disaccharides
  • beta-N-Acetylhexosaminidases
  • Acetylglucosamine