Solid-phase synthesis of amino amides and peptide amides with unnatural side chains

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. Thi...

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Bibliographic Details
Published in:Tetrahedron letters 2001-03, Vol.42 (11), p.2073-2076
Main Authors: Scott, William L, Delgado, Francisca, Lobb, Karen, Pottorf, Richard S, O'Donnell, Martin J
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)00090-9