Synthesis of mono- and di-hydroxylated prolines and 2-hydroxymethylpyrrolidines from non-carbohydrate precursors

Carbohydr Res. 2003 Oct 31;338(22):2265-90. doi: 10.1016/j.carres.2003.09.002.

Abstract

Natural and synthetic imino sugars are biologically important as glycosidase inhibitors. This review includes selected syntheses of 3-hydroxyproline, 4-hydroxyproline, 3,4-dihydroxyproline, 2-hydroxymethyl-3-hydroxypyrrolidine and 2-hydroxymethyl-pyrrolidine-3,4-diol, which exhibit glycosidase inhibitory and various other biological activities.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Arabinose
  • Carbohydrates / chemistry
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycoside Hydrolases / metabolism
  • Hydroxyproline / analogs & derivatives*
  • Hydroxyproline / chemical synthesis*
  • Hydroxyproline / chemistry
  • Hydroxyproline / isolation & purification
  • Imino Furanoses
  • Stereoisomerism
  • Sugar Alcohols / chemical synthesis*
  • Sugar Alcohols / chemistry

Substances

  • Carbohydrates
  • Imino Furanoses
  • Sugar Alcohols
  • 1,4-dideoxy-1,4-iminoarabinitol
  • Arabinose
  • Glycoside Hydrolases
  • Hydroxyproline