PHOTOREACTIVE ENKEPHALIN ANALOG - [D-ALA2,P-N3-PHE4-MET5]ENKEPHALIN - SYNTHESIS, PURIFICATION BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY AND CHARACTERIZATION

  • 1 January 1985
    • journal article
    • research article
    • Vol. 26  (1) , 63-69
Abstract
A photoreactive [D-Ala2, p-N3-Phe4-Met5] enkephalin was synthesized by classical solution peptide synthetic methods. The hydroxysuccinimide ester was used in all the coupling steps in the presence of a weak base, triethylamine. The deprotected enkephalin analog was purified on high performance liquid chromatography using a Waters, C18 .mu.Bondapak reverse phase column and its purity was assessed by TLC. The composition of the analog was determined and confirmed by elemental analysis and amino acid analysis. Its photoreactivity was demonstrated by the time-dependent UV spectral changes on exposure to light. Competition receptor binding showed that [D-Ala2, p-N3-Phe4-Met5] enkephalin was 4-fold more potent than [D-Ala2, Met5]-enkephalin in competing for binding to the enkephalin binding site. This photoreactive enkephalin analog may be suitable for use in the in situ photoaffinity labeling of the enkephalin receptor.