Characterization of cyclic peptides containing disulfide bonds

J Pharm Biomed Anal. 2015 May 10:109:112-20. doi: 10.1016/j.jpba.2015.01.009. Epub 2015 Jan 22.

Abstract

Unlike linear peptides, analysis of cyclic peptides containing disulfide bonds is not straightforward and demands indirect methods to achieve a rigorous proof of structure. Three peptides that belong to this category, p-Cl-Phe-DPDPE, DPDPE, and CTOP, were analyzed and the results are presented in this paper. The great potential of two dimensional NMR and ESI tandem mass spectrometry was harnessed during the course of peptide characterizations. A new RP-HPLC method for the analysis of trifluoroacetic acid is also presented. It is robust, simple, and efficient compared to the currently available methods.

Keywords: Opioid peptides; RP-HPLC; Tandem mass spectrometry; Trifluoroacetic acid; Two-dimensional NMR.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetic Acid / chemistry
  • Chromatography, High Pressure Liquid
  • Disulfides / chemistry*
  • Dithiothreitol / chemistry
  • Enkephalin, D-Penicillamine (2,5)- / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Peptides, Cyclic / chemistry*
  • Somatostatin / analogs & derivatives
  • Somatostatin / chemistry
  • Tandem Mass Spectrometry
  • Trifluoroacetic Acid

Substances

  • Disulfides
  • Indicators and Reagents
  • Peptides, Cyclic
  • phenylalanyl-cyclo(cysteinyltyrosyl-tryptophyl-ornithyl-threonyl-penicillamine)threoninamide
  • Somatostatin
  • Enkephalin, D-Penicillamine (2,5)-
  • Trifluoroacetic Acid
  • Acetic Acid
  • Dithiothreitol