Journal article
Carbocations in action. Design, synthesis and evaluation of a highly acid sensitive naphthalene based backbone amide linker for solid phase synthesis
Innate Immunology, Division of Veterinary Diagnostics and Research, National Veterinary Institute, Technical University of Denmark1
Division of Veterinary Diagnostics and Research, National Veterinary Institute, Technical University of Denmark2
National Veterinary Institute, Technical University of Denmark3
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 stabile alkoxy-substituted methyl naphthyl carbocation. [structure: see text]
Language: | English |
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Year: | 2006 |
Pages: | 5817-5820 |
ISSN: | 15237052 and 15237060 |
Types: | Journal article |
DOI: | 10.1021/ol062410j |
ORCIDs: | 0000-0002-3371-9500 and 0000-0002-7641-8302 |