Isolation and identification of peptide conformers by reversed-phase high-performance liquid chromatography and NMR at low temperature

Journal of Chromatography. a
A KálmánC Horváth

Abstract

Peptide conformers with one or more rotationally hindered peptide bonds due to the presence of proline and/or another N-substituted amino acid residue in the molecule were separated by reversed-phase chromatography at low temperatures, isolated and identified by NMR. The scope of this investigation included the cis-trans isomers of the dipeptides Leu-Pro, Phe-Pro and Tyr-Pro as well as conformers of opioid peptides containing proline and/or the proline-like Tic (1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid) residues: Tyr-Pro-Phe (beta-casomorphin 1-3 fragment), Tyr-Tic-Phe-Phe, Try-Pro-Phe-Pro-Gly (beta-casomorphin-5), Tyr-Tic-Phe-Phe-Val-Val-Gly-NH2 and Tyr-Tic-Phe-Gly-Tyr-Pro-Ser-NH2. Chromatography with micropellicular and totally porous octadecylated silica stationary phases and aqueous methanol under isocratic elution conditions resulted in well separated peaks of the rotational isomers at sufficiently low temperatures. Preparative RP-HPLC was carried out with eluents containing water and methanol, both deuterated, and the effluent fractions containing each isomer were collected for further investigation. The conformational states of the peptide isomers upon separation were conserved by storing the effluent fractions ...Continue Reading

References

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Citations

Feb 6, 2002·Chembiochem : a European Journal of Chemical Biology·E GaggelliG Valensin
Mar 29, 2000·Journal of Chromatography. a·H TrabelsiK Bouzouita
Jan 25, 2003·Journal of Biochemical and Biophysical Methods·S BouabdallahS Sabbah
Mar 20, 2003·Journal of Pharmaceutical and Biomedical Analysis·S BouabdallahR Khaddar
Feb 4, 2005·Electrophoresis·Carl I D Newman, Victoria L McGuffin
Apr 30, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·G AlouiN Giraud
Aug 18, 2020·Food Chemistry·Muthu ThiruvengadamUmadevi Subramanian
May 18, 2006·Bioconjugate Chemistry·Cécile ClavaudChristophe Dugave
Jun 15, 1997·Analytical Chemistry·A F HühmerC Schôneich
Jan 10, 2013·Journal of Agricultural and Food Chemistry·Giuseppe IacominoGianfranco Mamone
Apr 2, 2002·Analytical Chemistry·Jonathan D Thompson, Peter W Carr
Dec 31, 1997·Journal of Chromatography. a·A S Rathore, C Horváth
Sep 13, 1996·Journal of Chromatography. a·F ThuneckeC Horváth

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