Synthesis of peptide-N-alkylamides on a new PS-TTEGDA polymer support using photolabile anchoring group

Peptide-N-alkylamides were synthesised on a new highly solvating copolymer of 4% tetraethyleneglycol diacrylate-cross-linked polystyrene (PS-TTEGDA) s upport The polymer was synthesised by suspension polymerisation using a fre e radical initiator. The synthesis of C-terminal peptide-N-alkylamide invol ve prior incorporation of a photolabile linker, 3-nitro-4-bromo-methylbenzo ic acid to the aminomethylated support The N-alkylamino group act as an anc horing group for the peptide as well as a latent function for the C-termina l modification of the attached peptide. Irradiation of the peptide-resin wi th 350 nm light in TFE/DCM resulted in the release of peptide-N-alkylamides . Synthetic utility of the new support was demonstrated by the synthesis of Boc-amino acid-N-alkylamides and C-terminal peptide-N-alkyl amides in 75-8 0% yields and with high purity. (C) 1999 Elsevier Science Ltd. All rights r eserved.