Synthesis of 2-chloro-4-nitrophenyl alpha-L-fucopyranoside: a substrate for alpha-L-fucosidase (AFU)

Carbohydr Res. 2003 Jul 22;338(15):1603-7. doi: 10.1016/s0008-6215(03)00244-1.

Abstract

An effective method to prepare the substrate of alpha-L-fucosidase (AFU) is described. Ethyl 1-thiofucoside with a free 2-OH group was used as the glycosyl donor, and there was found no self-condensed side product. The use of the HF.pyridine reagent to remove the silyl protecting group in the last step afforded a target molecule of high purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glucosides / metabolism*
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Nitro Compounds / metabolism*
  • Substrate Specificity
  • alpha-L-Fucosidase / metabolism*

Substances

  • 2-chloro-4-nitrophenyl alpha-L-fucopyranoside
  • Glucosides
  • Nitro Compounds
  • alpha-L-Fucosidase