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p-Nitromandelic Acid as a Highly Acid-Stable Safety-Catch Linker for Solid-Phase Synthesis of Peptide and Depsipeptide Acids

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journal contribution
posted on 2007-04-12, 00:00 authored by Albert Isidro-Llobet, Mercedes Alvarez, Klaus Burger, Jan Spengler, Fernando Albericio
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 °C with 5% TFA in dioxane.

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