2'-Nitrobenzhydryl Polystyrene Resin: A New Photosensitive Polymeric Support for Peptide Synthesis

Article abstract of DOI:10.1021/jo00235a012

2'-Nitrobenzhydryl polystyrene resin (NBH-resin) was prepared from the commercially available styrene-divinylbenzene cross-linked polymer by a two-step polymer analogous reaction.This resin was employed as a photolytically cleavable polymeric protective support for carboxyl function in amino acids under neutral conditions.The 2'-nitrobenzhydryl resin possesses good stability in 4 N HCl-dioxane required for the deprotection of the temporary Nα-tert-butyloxycarbonyl protecting group.The advantage of the new resin over the already reported benzhydryl resin is its increased acid stability during the Nα deblocking, which permits the peptide synthesis with the commonly available Boc-amino acids.The applicability of this resin is illustrated with the solid-phase synthesis of some model peptides.