A new strategy for solid-phase synthesis of C-terminal peptide amides based on the use of N-tetrachlorophthaloyl protected amino acids with acid-labile side-chain protection is described.
Solid-phase synthesis of amino amides and peptide amides with unnatural side chains
β Scribed by William L Scott; Francisca Delgado; Karen Lobb; Richard S Pottorf; Martin J O'Donnell
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 86 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Unnatural amino amides and peptide amides can be synthesized, using solid-phase chemistry, from glycine attached directly (or through an intervening peptide sequence) to a Rink resin. The glycine is converted to an activated benzophenone imine derivative, followed by C-alkylation and hydrolysis. This sequence provides a mild, high yielding route to Rink resin-bound racemic, unnatural, amino amides and di-and tripeptide amides. Cleavage with trifluoroacetic acid provides the final amide products in good yield and purity.
π SIMILAR VOLUMES
Head-to-tail cyclic peptides with hybrid side-chains have been synthesized by solid-phase assembly of the linear sequences, followed by PyAOP/HOAt/DIEA-mediated cyclization either while resin-bound or, after cleavage, in solution.