Convenient enzymatic synthesis of a p-nitrophenyl oligosaccharide series of sialyl N-acetyllactosamine, sialyl Le x and relevant compounds

Carbohydr Res. 2005 Nov 21;340(16):2469-75. doi: 10.1016/j.carres.2005.08.019. Epub 2005 Oct 5.

Abstract

From the beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (1) prepared by the transglycosylation of beta-galactosidase from Bacillus circulans, alpha-D-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (9) and alpha-D-Neu5Ac-(2-->6)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p (10) were effectively synthesized with an equimolar ratio of CMP-Neu5Ac by recombinant rat alpha-(2-->3)-N-sialyltransferase and rat liver alpha-(2-->6)-N-sialyltransferase, respectively. The former enzyme also transferred effectively the Neu5Ac residue from CMP-Neu5Ac to the location of OH-3 in the non-reducing terminal of beta-D-Gal-(1-->4)-beta-D-Gal-OC6H4NO2-p or beta-D-Gal-(1-->4)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OC6H4NO2-p, while the latter enzyme did not. In the case of equimolar ratio of GDP-Fuc/acceptor, 1 and 9 were further fucosylated quantitatively to form beta-D-Gal-(1-->4)-beta-D-(alpha-l-Fuc-(1-->3)-)-GlcNAc-OC6H4NO2-p (14) and alpha-D-Neu5Ac-(2-->3)-beta-D-Gal-(1-->4)-beta-D-(alpha-l-Fuc-(1-->3)-)-GlcNAc-OC6H4NO2-p (13) by recombinant human alpha-(1-->3)-fucosyltransferase VII, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Animals
  • Bacillus / enzymology
  • Carbohydrate Sequence
  • Fucosyltransferases / chemistry
  • Humans
  • Lewis Blood Group Antigens
  • Molecular Sequence Data
  • Molecular Structure
  • Nitrophenols / chemistry
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Rats
  • Recombinant Proteins / genetics
  • Sialyl Lewis X Antigen
  • Sialyltransferases / chemistry
  • Transferases / chemistry*
  • beta-Galactosidase / chemistry*

Substances

  • Amino Sugars
  • Lewis Blood Group Antigens
  • Lewis a oligosaccharide
  • Nitrophenols
  • Oligosaccharides
  • Recombinant Proteins
  • Sialyl Lewis X Antigen
  • sialyl-N-acetyllactosamine
  • Transferases
  • FUT7 protein, human
  • Fucosyltransferases
  • Sialyltransferases
  • beta-Galactosidase