Solid-Phase Synthesis of N-Methyl- and N-Ethylamides of Peptides Using Photolytically Detachable ((3-Nitro-4-((alkylamino)methyl)benzamido)methyl)polystyrene Resin

Article abstract of DOI:10.1021/jo00296a049

A convenient method for the solid-phase synthesis of C-terminal peptide N-alkylamides using a photolytically detachable ((3-nitro-4-((alkylamino)methyl)benzamido)methyl)polystyrene support is described.The method involves prior incorporation of an alkylamine moiety into the ((3-nitro-4-(bromomethyl)benzamido)methyl)polystyrene resin, on which the peptides were assembled and subsequently cleaved in the form of the peptide N-alkylamides by photolysis.The N-alkylamino group acts as an anchoring function for the peptide as well as a latent reagent function for the C-terminal modification of the attached peptide.The method is particularly useful if the peptide contains Asp or Glu with a benzyl ester side chain protecting group.The synthetic applicability of the mehtod is illustrated with the solid-phase synthesis of N-alkylamides of a few model peptides in 70-77percent yields and analogues of the luteinizing hormone-releasing hormone in 48-56percent yield.