Propargylamine-isothiocyanate reaction: efficient conjugation chemistry in aqueous media

Chem Commun (Camb). 2014 Jul 25;50(58):7800-2. doi: 10.1039/c4cc00863d.

Abstract

A coupling reaction between secondary propargyl amines and isothiocyanates in aqueous media is described. The reaction is high-yielding and affords cyclized products within 2-24 h. A functionalized ether lipid was synthesized in 8 steps, formulated as liposomes with POPC and conjugated to FITC under mild conditions using this method.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Cyclization
  • Isothiocyanates / chemistry*
  • Pargyline / analogs & derivatives*
  • Pargyline / chemistry
  • Propylamines / chemistry*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Thiazolidines / chemical synthesis

Substances

  • Isothiocyanates
  • Propylamines
  • Thiazolidines
  • propargylamine
  • isothiocyanic acid
  • Pargyline