Endohexosaminidase-catalysed glycosylation with oxazoline donors: effects of organic co-solvent and pH on reactions catalysed by Endo A and Endo M

Carbohydr Res. 2009 Dec 14;344(18):2433-8. doi: 10.1016/j.carres.2009.09.013. Epub 2009 Sep 18.

Abstract

The synthetic efficiency of endohexosaminidase-catalysed glycosylation reactions using N-glycan oxazolines as donors was investigated as two reaction parameters were varied. Both the addition of quantities of an organic co-solvent and modulation of reaction pH between 6.5 and 8.0 were found to have different effects on reactions catalysed by either Endo A (and two available mutants) or Endo M, indicating subtle differences between these two family GH85 enzymes. Fine tuning of reaction pH, or the addition of quantities of an organic co-solvent, resulted in beneficial increases in achievable synthetic efficiency by effecting a reduction in the rate of competitive hydrolytic processes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glycosylation
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / metabolism*
  • Organic Chemicals / chemical synthesis
  • Oxazoles / chemistry
  • Oxazoles / metabolism*
  • Solvents

Substances

  • Organic Chemicals
  • Oxazoles
  • Solvents
  • Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase