Organic letters

Carbocations in action. Design, synthesis, and evaluation of a highly acid-sensitive naphthalene-based backbone amide linker for solid-phase synthesis

M Pittelkow, U Boas, JB Christensen

Index: Pittelkow, Michael; Boas, Ulrik; Christensen, Jorn B. Organic Letters, 2006 , vol. 8, # 25 p. 5817 - 5820

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Citation Number: 10

Abstract

The design, synthesis, and properties of an extremely acid-labile backbone amide linker based on a regiospecifically substituted tetraalkoxy naphthaldehyde core are presented. This handle enables cleavage of peptide backbone amides (secondary amides) off a solid support using as little as 0.5% TFA in CH2Cl2. This proceeds without cleavage of tert-butyl ethers and tert-butyl esters. The design is based on a DFT study that predicted the most ...