p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids.
[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.
Isidro-Llobet
Albert
A
Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1-5, E-08028 Barcelona, Spain.
Alvarez
Mercedes
M
Burger
Klaus
K
Spengler
Jan
J
Albericio
Fernando
F
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
D000143:Acids; D003432:Cross-Linking Reagents; D008333:Mandelic Acids; D009574:Nitro Compounds; D010455:Peptides; C520237:p-nitromandelic acid