Concise synthesis of glyconoamidines as affinity ligands for the purification of β-glucosidase involved in control of some biological events including plant leaf movement

Eisuke Kato, Tadahiro Kumagai, Minoru Ueda

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Glycosidases are involved in deactivation or storage of some endogenous bioactive substances through biologically intriguing processes. For example, nyctinastic leaf movement is controlled by a biological clock through the regulation of β-glucosidase activity. Ganem's glyconoamidine (1) is used as a micromolar inhibitor of glucosidase in biochemical studies and would be useful as an affinity ligand for purification of glycosidase. However, its use for the specific inhibition of glucosidase which is highly specific to a glycoside with voluntary aglycon is seriously restricted because no universal method for the synthesis of N-alkylated glyconoamidine has been reported. Here, we report a concise synthesis of N-alkylated Ganem's glyconoamidine with voluntary aglycon using a non-protected sugar derivative.

Original languageEnglish
Pages (from-to)4865-4869
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number29
DOIs
Publication statusPublished - 2005 Jul 18

Keywords

  • Glucosidase
  • Inhibitor
  • Nyctinasty

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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