title: p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids.
abstract: [reaction: see text] p-Nitromandelic acid as a safety-catch linker for Boc/Bzl-SPPS of base-labile compounds like peptides and depsipeptides is described. This linker permits acidic removal of side-chain protection groups from the resin. For cleavage from the solid support, the p-nitro group was reduced with tin(II) chloride. After washing off the reducing agents, the (depsi)peptide acids with or without the side-chain protection schemes were obtained by microwave irradiation at 50 degrees C with 5% TFA in dioxane.
authors: Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1-5, E-08028 Barcelona, Spain.
authors: Albert
authors: A
authors: Isidro-Llobet
authors: Mercedes
authors: M
authors: Alvarez
authors: Klaus
authors: K
authors: Burger
authors: Jan
authors: J
authors: Spengler
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D000143:Acids / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D008333:Mandelic Acids / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000143:Acids; D003432:Cross-Linking Reagents; D008333:Mandelic Acids; D009574:Nitro Compounds; D010455:Peptides; C520237:p-nitromandelic acid