Edman chemistry reactions

The chemistry of this reaction has been extensively studied by Use and Edman. Although the reaction velocity is different for various amino acids, the reaction is complete in 1 N HCl at 80 °C within 10 min, with virtually all amino acids. This treatment, however, would cause partial hydrolysis of the remaining peptide. The method was made amenable to automation when Edman suggested to separate the thiazolinone derivative from the remaining peptide by extraction of the liberated thiazolinone derivative into butyl chloride and to perform the conversion into the PTH-amino acid outside the reaction vessel. 

Recently, Laursen realized the concept of a novel Peptide-Sequencer based on the chemistry of the Edman degradation, adapted to solid phase chemistry. The peptide under investigation is covalently linked to a resin packed into a column. The reactions are carried out by pumping the reagents and solvents through the column as required. This method appears to be particularly suitable for shorter peptides and may be regarded as an excellent supplement to the Sequencer based on Edman s design. 

Figure 5-2. Chemistry of the Edman degradation. In the Edman degradation, peptides undergo reaction with phenylisothiocyanate which generates a phenylthiocarbamylpeptide adduct. This adduct is cleaved to release the...

PITC chemistry is becoming increasingly popular for the analysis of amino acids. This is extracted from the Edman degradation chemistry. The reaction scheme is illustrated in Figure 3. The most popular... 

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