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Carbocations in action. Design, synthesis, and evaluation of a highly acid-sensitive naphthalene-based backbone amide linker for solid-phase synthesis.
- Source :
-
Organic letters [Org Lett] 2006 Dec 07; Vol. 8 (25), pp. 5817-20. - Publication Year :
- 2006
-
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 stabile alkoxy-substituted methyl naphthyl carbocation. [structure: see text]
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 8
- Issue :
- 25
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 17134280
- Full Text :
- https://doi.org/10.1021/ol062410j