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Edman Degradation

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr206

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Edman Degradation. Comprehensive Organic Name Reactions and Reagents. 206:954–958.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The reaction between phenyl isothiocyanate and the free amino group of the N-terminal amino acid within a polypeptide to generate a thiourea, which upon the intramolecular cyclization via the nucleophilic addition of the amino group to adjacent amide carbonyl cleaves the N-terminal amino acids as a phenylthiohydantoin derivative and leaves the second amino acid as the N-terminus again, is generally known as the Edman degradation. This method shows a few disadvantages and, to overcome these weaknesses, the reaction has been carried out by means of solid-phase support synthesis (SPSS). Further development has made this degradation valuable for sequencing the C-terminal segments of hydroxyethylamine-derived peptides and a useful method for the synthesis of 2-iminohydantoins.

Keywords:

  • phenylthiohydantoin derivatives;
  • solid-phase support synthesis (SPSS);
  • 2-iminohydantoins;
  • hydroxyethylamine-derived peptides