Facile synthesis toward the construction of an activity probe library for glycosidases

Tong Hong Shie, Ying Ling Chiang, Jing Jer Lin*, Yaw-Kuen Li, Lee Chiang Lo

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Chemical probes that selectively label the glycoside hydrolase (GH) subfamilies have proven to be a powerful tool in GH-related research. We have previously demonstrated the design and synthesis of an activity probe for β-glucosidase adopting a cassette-like design in a model study. Herein we report an improved synthetic route using (4-hydroxyphenyl)acetic acid 2-cyanoethyl ester as the precursor for the latent trapping device. Parallel syntheses were performed for the preparation of a library based on the structure of a key intermediate. The recognition head of this library covers a series of six sugars, including α- and β-D-Glc, α- and β-D-Gal, α-D-Man, and α-L-Fuc. Each member in this versatile intermediate library could serve as the building block in constructing an activity probe for GHs. As demonstrated in this study, three probes that have the 1,2-cis configuration were thus prepared for the first time to target α-D-glucosidase, α-D-galactosidase, and α-L-fucosidase, respectively.

Original languageEnglish
Pages (from-to)443-456
Number of pages14
JournalCarbohydrate Research
Volume341
Issue number4
DOIs
StatePublished - 20 Mar 2006

Keywords

  • Activity probe
  • Biotin
  • Carbohydrate
  • Glycosidase
  • Hydrolase
  • Mechanism-based labeling
  • Proteomics

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