Org Lett. 2007 Apr 12;9(8):1429-32. Epub 2007 Mar 17.

p-Nitromandelic acid as a highly acid-stable safety-catch linker for solid-phase synthesis of peptide and depsipeptide acids.

Isidro-Llobet A, Alvarez M, Burger K, Spengler J, Albericio F.

Source

Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1-5, E-08028 Barcelona, Spain.

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.

PMID:: 17367151; [PubMed - indexed for MEDLINE]

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