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Abstract
We report a method for the simultaneous determination of the sequence and absolute configuration of peptide amino acids using a combination of Edman degradation and HPLC–MS/CD. Phenylthiohydantoin (PTH) derivatives of 20 pairs of standard d- and l-amino acids were synthesized by the Edman reaction. The CD spectra of the derivatives revealed that each pair of the PTH derivatives exhibited the absorption with opposite signs at around 270 nm. These standard PTH derivatives showed well-resolved resolution without interference from byproducts in the ion chromatogram and clear positive/negative CD absorptions when subjected on a reversed phase HPLC–MS system coupled with a CD-2095 HPLC detector. This method was applied for the detection of a synthetic pentapeptide and a natural depsipeptide (halicylindramide C). The sequence and configuration of the pentapeptide and up to eight residues of halicylindramide C were successfully analyzed by this method. The amino acid configuration of the pentapeptide was also determined successfully by subjecting its acid hydrolysates to the Edman reaction followed by HPLC–MS/CD.
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1 Kyungpook National University, School of Food Science and Biotechnology & Department of Integrative Biotechnology, Daegu, South Korea (GRID:grid.258803.4) (ISNI:0000 0001 0661 1556)
2 Seoul National University, Laboratory of Marine Drugs, School of Earth and Environmental Sciences, Seoul, South Korea (GRID:grid.31501.36) (ISNI:0000 0004 0470 5905); Seoul National University, Research Institute of Oceanography, Seoul, South Korea (GRID:grid.31501.36) (ISNI:0000 0004 0470 5905)
3 Yeungnam University, College of Pharmacy, Gyeongsan-si, South Korea (GRID:grid.413028.c) (ISNI:0000 0001 0674 4447)
4 Seoul National University, Laboratory of Marine Drugs, School of Earth and Environmental Sciences, Seoul, South Korea (GRID:grid.31501.36) (ISNI:0000 0004 0470 5905); Seoul National University, Research Institute of Oceanography, Seoul, South Korea (GRID:grid.31501.36) (ISNI:0000 0004 0470 5905); Seoul National University, Interdisciplinary Graduate Program in Genetic Engineering, Seoul, South Korea (GRID:grid.31501.36) (ISNI:0000 0004 0470 5905)