Photocleavable 2-nitrobenzylamino anchored polystyrene-butanediol dimethacrylate supports for the synthesis of protected peptides, peptide amides andpeptide N-alkyl amides

2-Nitrobenzylamino-type anchoring groups were incorporated on 2% butanediol dimethacrylate cross-linked polystyrene support. The resultant photolabile polymeric supports were used for the synthesis of fully protected peptides and their final cleavage as C-terminal peptide acids, peptide amides and p eptide N-alkyl amides by photolysis under mild neutral conditions. The phot osensitive chromophore has a dual function of serving as an anchoring linka ge between the support and the growing peptide chain and as a latent reagen t for the conversion of a C-terminal carboxyl group into the modified form during photolytic cleavage. The C-terminal modified peptides were obtained by irradiating the peptidyl resin in a TFE/DCM mixture at 350 nm. The effic acy of the new resin is illustrated by synthesizing the protected derivativ es of the peptides in very high yield and purity. The identity of the pepti des was checked by amino acid analysis, TLC and MALDI TOF MS. (C) 2001 Else vier Science Ltd. AU rights reserved.